CN88103009A - 环状抗凝血肽的制备方法 - Google Patents

环状抗凝血肽的制备方法 Download PDF

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Publication number: CN88103009A
Authority: CN; China
Prior art keywords: amino; amino acid; glu; alanine; peptide
Prior art date: 1987-05-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

CN198888103009A

Other languages

English (en)

Chinese (zh)

Inventor

克斯坦安斯凯·约翰·李

奥·西蒙杰·提

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi Aventis UK Holdings Ltd

Original Assignee

Merrell Dow Pharmaceuticals Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-05-21

Filing date

1988-05-21

Publication date

1988-12-21

1988-05-21 Application filed by Merrell Dow Pharmaceuticals Ltd filed Critical Merrell Dow Pharmaceuticals Ltd

1988-12-21 Publication of CN88103009A publication Critical patent/CN88103009A/zh

Status Pending legal-status Critical Current

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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000004899 c-terminal region Anatomy 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001734 carboxylic acid salts Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000010367 cloning Methods 0.000 description 1
230000035602 clotting Effects 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
150000001912 cyanamides Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
150000001945 cysteines Chemical class 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000011033 desalting Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
MQYQOVYIJOLTNX-UHFFFAOYSA-N dichloromethane;n,n-dimethylformamide Chemical compound ClCCl.CN(C)C=O MQYQOVYIJOLTNX-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
208000009190 disseminated intravascular coagulation Diseases 0.000 description 1
PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
229950003499 fibrin Drugs 0.000 description 1
229940012952 fibrinogen Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
UHBYWPGGCSDKFX-VKHMYHEASA-N gamma-carboxy-L-glutamic acid Chemical compound OC(=O)[C@@H](N)CC(C(O)=O)C(O)=O UHBYWPGGCSDKFX-VKHMYHEASA-N 0.000 description 1
108010063718 gamma-glutamylaspartic acid Proteins 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
235000004554 glutamine Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
235000014304 histidine Nutrition 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
150000002462 imidazolines Chemical class 0.000 description 1
238000002513 implantation Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
238000005304 joining Methods 0.000 description 1
150000004658 ketimines Chemical class 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
SOOARYARZPXNAL-UHFFFAOYSA-N methyl-thiophenol Natural products CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
229960001639 penicillamine Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
238000011458 pharmacological treatment Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
150000002994 phenylalanines Chemical class 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
235000013930 proline Nutrition 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003219 pyrazolines Chemical class 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
210000003079 salivary gland Anatomy 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000010532 solid phase synthesis reaction Methods 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000009424 thromboembolic effect Effects 0.000 description 1
230000001732 thrombotic effect Effects 0.000 description 1
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 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
- C07K7/64—Cyclic peptides containing only normal peptide links
- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Biophysics (AREA)
Diabetes (AREA)
Hematology (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Tropical Medicine & Parasitology (AREA)
Gastroenterology & Hepatology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Polyesters Or Polycarbonates (AREA)

CN198888103009A 1987-05-21 1988-05-21 环状抗凝血肽的制备方法 Pending CN88103009A (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5320487A	1987-05-21	1987-05-21
US053,204		1987-05-21

Publications (1)

Publication Number	Publication Date
CN88103009A true CN88103009A (zh)	1988-12-21

Family

ID=21982612

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN198888103009A Pending CN88103009A (zh)	1987-05-21	1988-05-21	环状抗凝血肽的制备方法

Country Status (17)

Country	Link
EP (1)	EP0291981B1 (2)
JP (1)	JP2598302B2 (2)
KR (1)	KR880013977A (2)
CN (1)	CN88103009A (2)
AT (1)	ATE88190T1 (2)
AU (1)	AU608846B2 (2)
CA (1)	CA1328540C (2)
DE (1)	DE3880194T2 (2)
DK (1)	DK278588A (2)
ES (1)	ES2054732T3 (2)
FI (1)	FI89064C (2)
HU (1)	HU198512B (2)
IL (1)	IL86439A (2)
NO (1)	NO882239L (2)
NZ (1)	NZ224677A (2)
PT (1)	PT87537B (2)
ZA (1)	ZA883444B (2)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5236898A (en) *	1987-05-21	1993-08-17	Merrell Dow Pharmaceuticals Inc.	Cyclic anticoagulant peptides
ZA883444B (2) *	1987-05-21	1988-11-16
US5192745A (en) *	1987-05-21	1993-03-09	Merrell Dow Pharmaceuticals Inc.	Cyclic anticoagulant peptides
NZ228995A (en) *	1988-05-10	1992-03-26	Merrell Dow Pharma	Hirudin peptide derivatives and pharmaceutical compositions
US5196404B1 (en) *	1989-08-18	1996-09-10	Biogen Inc	Inhibitors of thrombin
US5240913A (en) *	1989-08-18	1993-08-31	Biogen, Inc.	Inhibitors of thrombin
US5192747A (en) *	1989-10-03	1993-03-09	Merrell Dow Pharmaceuticals Inc.	Anticoagulant peptides
CA2026377A1 (en) *	1989-10-03	1991-04-04	John L. Krstenansky	Radiolabeled anticoagulant peptides
CA2035917C (en) *	1990-02-13	2001-10-02	John L. Krstenansky	Stabilized sulfonate, sulfate, phosphonate and phosphate derivatives of hirudin
US5242810A (en) *	1990-12-07	1993-09-07	Biogen, Inc.	Bifunctional inhibitors of thrombin and platelet activation
DE4103649A1 (de) *	1991-02-07	1992-08-13	Basf Ag	Neue antikoagulatorisch wirksame peptide
US5516889A (en) *	1993-06-21	1996-05-14	University Technologies International, Inc.	Synthetic thrombin receptor peptides
US7410457B2 (en)	2003-08-08	2008-08-12	Westfalia Separator Ag	Separator with a disc stack with rising channels and non-radial distributor channels
CN104054441A (zh) *	2014-06-30	2014-09-24	泰州樱田农机制造有限公司	撒肥机排料调节装置
CN110981953B (zh) *	2019-12-13	2021-10-08	首都医科大学	一种多肽和多肽的应用及包含多肽的组合物

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA883444B (2) *	1987-05-21	1988-11-16

1988
- 1988-05-16 ZA ZA883444A patent/ZA883444B/xx unknown
- 1988-05-16 CA CA000566915A patent/CA1328540C/en not_active Expired - Fee Related
- 1988-05-17 AU AU16343/88A patent/AU608846B2/en not_active Ceased
- 1988-05-18 NZ NZ224677A patent/NZ224677A/xx unknown
- 1988-05-19 DE DE8888108047T patent/DE3880194T2/de not_active Expired - Fee Related
- 1988-05-19 EP EP88108047A patent/EP0291981B1/en not_active Expired - Lifetime
- 1988-05-19 PT PT87537A patent/PT87537B/pt not_active IP Right Cessation
- 1988-05-19 FI FI882359A patent/FI89064C/fi not_active IP Right Cessation
- 1988-05-19 AT AT88108047T patent/ATE88190T1/de active
- 1988-05-19 KR KR1019880005871A patent/KR880013977A/ko not_active Ceased
- 1988-05-19 ES ES88108047T patent/ES2054732T3/es not_active Expired - Lifetime
- 1988-05-19 IL IL86439A patent/IL86439A/xx unknown
- 1988-05-20 HU HU882615A patent/HU198512B/hu not_active IP Right Cessation
- 1988-05-20 NO NO882239A patent/NO882239L/no unknown
- 1988-05-20 JP JP63122189A patent/JP2598302B2/ja not_active Expired - Fee Related
- 1988-05-20 DK DK278588A patent/DK278588A/da not_active Application Discontinuation
- 1988-05-21 CN CN198888103009A patent/CN88103009A/zh active Pending

Also Published As

Publication number	Publication date
FI882359A7 (fi)	1988-11-22
NZ224677A (en)	1990-08-28
PT87537B (pt)	1992-09-30
CA1328540C (en)	1994-04-12
JPS63307895A (ja)	1988-12-15
DE3880194D1 (de)	1993-05-19
AU1634388A (en)	1988-11-24
FI89064C (fi)	1993-08-10
FI882359A0 (fi)	1988-05-19
KR880013977A (ko)	1988-12-22
DE3880194T2 (de)	1993-08-26
IL86439A (en)	1992-11-15
EP0291981A3 (en)	1990-07-04
FI89064B (fi)	1993-04-30
DK278588D0 (da)	1988-05-20
AU608846B2 (en)	1991-04-18
PT87537A (pt)	1989-05-31
ATE88190T1 (de)	1993-04-15
JP2598302B2 (ja)	1997-04-09
NO882239L (no)	1988-11-22
EP0291981A2 (en)	1988-11-23
IL86439A0 (en)	1988-11-15
ES2054732T3 (es)	1994-08-16
HU198512B (en)	1989-10-30
NO882239D0 (no)	1988-05-20
EP0291981B1 (en)	1993-04-14
ZA883444B (2)	1988-11-16
DK278588A (da)	1988-11-22
HUT47136A (en)	1989-01-30

Legal Events

Date	Code	Title
1988-12-21	C06	Publication
1988-12-21	PB01	Publication
1990-08-29	C10	Entry into substantive examination
1990-08-29	SE01	Entry into force of request for substantive examination
1995-08-02	C01	Deemed withdrawal of patent application (patent law 1993)
1995-08-02	WD01	Invention patent application deemed withdrawn after publication

Publication	Publication Date	Title
KR960014105B1 (ko)	1996-10-14	항응혈성 펩티드
CN88103015A (zh)	1988-12-21	环状抗凝血剂肽
FI89064C (fi)	1993-08-10	Foerfarande foer framstaellning av peptidderivat av hirudin som hindrar koagulationen i blod
JP2916164B2 (ja)	1999-07-05	抗凝固剤ペプチドアルコール類
JP2899391B2 (ja)	1999-06-02	抗凝固ペプチド
JP2899430B2 (ja)	1999-06-02	安定化されたヒルディンのスルホネ−ト、サルフェ−ト、ホスホネ−ト、及びホスフェ−ト誘導体
JP2916182B2 (ja)	1999-07-05	凝固防止剤ペプチド類
JP3111075B2 (ja)	2000-11-20	抗凝固ペプチド
JP3264283B2 (ja)	2002-03-11	血小板凝集阻害活性を有するヒルディンの類似体
US5236898A (en)	1993-08-17	Cyclic anticoagulant peptides
US5192745A (en)	1993-03-09	Cyclic anticoagulant peptides
US6005071A (en)	1999-12-21	Anticoagulant peptides