JP2606528B2 - 新規ペプチド化合物またはその塩類 - Google Patents
新規ペプチド化合物またはその塩類Info
- Publication number
- JP2606528B2 JP2606528B2 JP4118870A JP11887092A JP2606528B2 JP 2606528 B2 JP2606528 B2 JP 2606528B2 JP 4118870 A JP4118870 A JP 4118870A JP 11887092 A JP11887092 A JP 11887092A JP 2606528 B2 JP2606528 B2 JP 2606528B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- alkyl
- formula
- salt
- Prior art date
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 266
- 150000003839 salts Chemical class 0.000 title claims abstract description 63
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 112
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 53
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 38
- 125000001424 substituent group Chemical group 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 14
- -1 4-amidinophenyl group Chemical group 0.000 claims description 160
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 238000003379 elimination reaction Methods 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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- 239000005557 antagonist Substances 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
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- 125000003107 substituted aryl group Chemical group 0.000 claims 1
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- 239000007858 starting material Substances 0.000 description 84
- 238000004949 mass spectrometry Methods 0.000 description 58
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
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- 239000002585 base Substances 0.000 description 6
- 125000001589 carboacyl group Chemical group 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 230000000069 prophylactic effect Effects 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
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- 102000003978 Tissue Plasminogen Activator Human genes 0.000 description 5
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- 150000007513 acids Chemical class 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 210000001715 carotid artery Anatomy 0.000 description 5
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
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- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
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- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- GAPYKZAARZMMGP-UHFFFAOYSA-N pyridin-1-ium;acetate Chemical compound CC(O)=O.C1=CC=NC=C1 GAPYKZAARZMMGP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960002898 threonine Drugs 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 238000007631 vascular surgery Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/745—Blood coagulation or fibrinolysis factors
- C07K14/75—Fibrinogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1019—Tetrapeptides with the first amino acid being basic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Hematology (AREA)
- Gastroenterology & Hepatology (AREA)
- Toxicology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919110298A GB9110298D0 (en) | 1991-05-13 | 1991-05-13 | New peptide compound and a process for the preparation thereof |
| GB91102988 | 1992-02-03 | ||
| GB92022607 | 1992-02-03 | ||
| GB929202260A GB9202260D0 (en) | 1992-02-03 | 1992-02-03 | New peptide compound and a process for the preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05148207A JPH05148207A (ja) | 1993-06-15 |
| JP2606528B2 true JP2606528B2 (ja) | 1997-05-07 |
Family
ID=26298895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4118870A Expired - Lifetime JP2606528B2 (ja) | 1991-05-13 | 1992-05-12 | 新規ペプチド化合物またはその塩類 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5574016A (enExample) |
| EP (1) | EP0513675B1 (enExample) |
| JP (1) | JP2606528B2 (enExample) |
| KR (1) | KR920021579A (enExample) |
| CN (2) | CN1043647C (enExample) |
| AT (1) | ATE142641T1 (enExample) |
| AU (1) | AU662522B2 (enExample) |
| CA (1) | CA2068478A1 (enExample) |
| DE (1) | DE69213546T2 (enExample) |
| DK (1) | DK0513675T3 (enExample) |
| ES (1) | ES2091359T3 (enExample) |
| GR (1) | GR3021182T3 (enExample) |
| HU (2) | HUT61780A (enExample) |
| IL (1) | IL101839A (enExample) |
| TW (1) | TW203057B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5272162A (en) * | 1992-07-02 | 1993-12-21 | G. D. Searle & Co. | Platelet aggregation inhibitors |
| US5354738A (en) * | 1992-09-04 | 1994-10-11 | G. D. Searle & Co. | Platelet aggregation inhibitors |
| US5314902A (en) * | 1993-01-27 | 1994-05-24 | Monsanto Company | Urea derivatives useful as platelet aggregation inhibitors |
| DE4309867A1 (de) * | 1993-03-26 | 1994-09-29 | Cassella Ag | Neue Harnstoffderivate, ihre Herstellung und Verwendung |
| EP0690847A1 (en) * | 1993-03-29 | 1996-01-10 | Zeneca Limited | Heterocyclic compounds as platelet aggregation inhibitors |
| US5652242A (en) * | 1993-03-29 | 1997-07-29 | Zeneca Limited | Heterocyclic derivatives |
| US5750754A (en) * | 1993-03-29 | 1998-05-12 | Zeneca Limited | Heterocyclic compounds |
| ES2159798T3 (es) * | 1993-03-29 | 2001-10-16 | Astrazeneca Ab | Derivados heterociclicos como inhibidores de la agregacion plaquetaria. |
| US5753659A (en) * | 1993-03-29 | 1998-05-19 | Zeneca Limited | Heterocyclic compouds |
| US5463011A (en) * | 1993-06-28 | 1995-10-31 | Zeneca Limited | Acid derivatives |
| GB9313285D0 (en) * | 1993-06-28 | 1993-08-11 | Zeneca Ltd | Acid derivatives |
| GB9313268D0 (en) * | 1993-06-28 | 1993-08-11 | Zeneca Ltd | Chemical compounds |
| US5780590A (en) * | 1993-10-15 | 1998-07-14 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Antithrombotic azacycloalkylalkanoyl peptides and pseudopeptides |
| JPH09505290A (ja) * | 1993-11-19 | 1997-05-27 | ジー．ディー．サール アンド カンパニー | Ｎ‐［Ｎ‐［５‐［４‐（アミノイミノメチル）フェニル］‐１‐オキソペンチル］‐Ｌ‐α‐アスパルチル］‐Ｌ‐フェニルアラニンまたはそのエステル並びにそれらの医薬的に許容される塩類の経皮的組成物 |
| US6387880B1 (en) | 1994-10-24 | 2002-05-14 | G.D. Searle & Co. | Transdermal N-[N-[5-[4-(aminoiminomethly)phenyl]-1-oxopentyl]-L-α-aspartyl]-L-phenylalainine or its esters and their pharmaceutically acceptable salts |
| EP0790247A4 (en) * | 1994-11-01 | 2000-07-19 | Terumo Corp | TETRAHYDROISOCHINOLINE DERIVATIVES AND MEDICINAL PRODUCTS CONTAINING THEM |
| US5766932A (en) * | 1995-12-20 | 1998-06-16 | Hoechst Marion Roussel, Inc. | Process for preparing N-acetyl(L)-4-cyanophenylalanine from a mixture of the corresponding D,L ethyl esters using subtilisin |
| CN1087349C (zh) * | 1995-12-20 | 2002-07-10 | 阿温蒂斯药物公司 | N－乙酰基－(L)－4－氰基苯丙氨酸Ac-(L)-Phe(4－CN)－OH与N－乙酰基－(L)－对脒基苯丙氨酸－环己基甘氨酸－β－（3－N－甲基吡啶鎓）－丙氨酸AC－（L）－PAPh－chg－PaIMe(3)-NH2的新颖的制备方法 |
| JP2001131078A (ja) * | 1999-11-09 | 2001-05-15 | Iatron Lab Inc | 新規活性固定化血小板及びその製造方法 |
| DE10005631A1 (de) | 2000-02-09 | 2001-08-23 | Max Planck Gesellschaft | Arginin-Mimetika als Faktor X¶a¶-Inhibitoren |
| CA2421575C (en) * | 2000-09-06 | 2011-07-12 | Emisphere Technologies, Inc. | Cyanophenoxy carboxylic acid compounds and compositions for delivering active agents |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4857508A (en) * | 1987-12-03 | 1989-08-15 | Monsanto Company | Novel platelet-aggregation inhibitor peptide derivatives |
| US5039805A (en) * | 1988-12-08 | 1991-08-13 | Hoffmann-La Roche Inc. | Novel benzoic and phenylacetic acid derivatives |
| CA2008116C (en) * | 1989-02-23 | 2001-11-20 | Thomas Weller | Glycine derivatives |
| CA2037153A1 (en) * | 1990-03-09 | 1991-09-10 | Leo Alig | Acetic acid derivatives |
| AU646838B2 (en) * | 1990-03-09 | 1994-03-10 | F. Hoffmann-La Roche Ag | Acetic acid derivatives |
| AU662142B2 (en) * | 1991-03-06 | 1995-08-24 | G.D. Searle & Co. | Phenyl amidines derivatives useful as platelet aggregation inhibitors |
| DE4212304A1 (de) * | 1992-04-13 | 1993-10-14 | Cassella Ag | Asparaginsäurederivate, ihre Herstellung und Verwendung |
-
1992
- 1992-05-08 EP EP92107757A patent/EP0513675B1/en not_active Expired - Lifetime
- 1992-05-08 AU AU16144/92A patent/AU662522B2/en not_active Ceased
- 1992-05-08 AT AT92107757T patent/ATE142641T1/de not_active IP Right Cessation
- 1992-05-08 DK DK92107757.4T patent/DK0513675T3/da active
- 1992-05-08 ES ES92107757T patent/ES2091359T3/es not_active Expired - Lifetime
- 1992-05-08 DE DE69213546T patent/DE69213546T2/de not_active Expired - Fee Related
- 1992-05-11 TW TW081103635A patent/TW203057B/zh active
- 1992-05-12 KR KR1019920007969A patent/KR920021579A/ko not_active Ceased
- 1992-05-12 CN CN92103241A patent/CN1043647C/zh not_active Expired - Fee Related
- 1992-05-12 IL IL10183992A patent/IL101839A/en not_active IP Right Cessation
- 1992-05-12 CA CA002068478A patent/CA2068478A1/en not_active Abandoned
- 1992-05-12 HU HU9201578A patent/HUT61780A/hu unknown
- 1992-05-12 JP JP4118870A patent/JP2606528B2/ja not_active Expired - Lifetime
-
1995
- 1995-05-22 US US08/446,288 patent/US5574016A/en not_active Expired - Fee Related
- 1995-06-22 HU HU95P/P00352P patent/HU211266A9/hu unknown
- 1995-08-18 CN CN95109813A patent/CN1120047A/zh active Pending
-
1996
- 1996-09-27 GR GR960402534T patent/GR3021182T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW203057B (enExample) | 1993-04-01 |
| US5574016A (en) | 1996-11-12 |
| CA2068478A1 (en) | 1992-11-14 |
| DE69213546D1 (de) | 1996-10-17 |
| IL101839A (en) | 1996-12-05 |
| ES2091359T3 (es) | 1996-11-01 |
| CN1066660A (zh) | 1992-12-02 |
| HU9201578D0 (en) | 1992-08-28 |
| HUT61780A (en) | 1993-03-01 |
| DE69213546T2 (de) | 1997-02-27 |
| GR3021182T3 (en) | 1996-12-31 |
| DK0513675T3 (da) | 1996-09-30 |
| EP0513675B1 (en) | 1996-09-11 |
| IL101839A0 (en) | 1992-12-30 |
| HU211266A9 (en) | 1995-11-28 |
| ATE142641T1 (de) | 1996-09-15 |
| AU662522B2 (en) | 1995-09-07 |
| JPH05148207A (ja) | 1993-06-15 |
| KR920021579A (ko) | 1992-12-18 |
| AU1614492A (en) | 1992-11-19 |
| CN1043647C (zh) | 1999-06-16 |
| CN1120047A (zh) | 1996-04-10 |
| EP0513675A1 (en) | 1992-11-19 |
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