CN1168142A - 新肽及其制备方法和用途 - Google Patents
新肽及其制备方法和用途 Download PDFInfo
- Publication number
- CN1168142A CN1168142A CN96191447A CN96191447A CN1168142A CN 1168142 A CN1168142 A CN 1168142A CN 96191447 A CN96191447 A CN 96191447A CN 96191447 A CN96191447 A CN 96191447A CN 1168142 A CN1168142 A CN 1168142A
- Authority
- CN
- China
- Prior art keywords
- gly
- pro
- aap10
- ala
- peptide
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 108090000765 processed proteins & peptides Proteins 0.000 title description 22
- 102000004196 processed proteins & peptides Human genes 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 201000010099 disease Diseases 0.000 claims abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical group NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000004471 Glycine Chemical group 0.000 claims description 4
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- NGCVFIUAYANGKF-QMMMGPOBSA-N (2s)-3-(4-hydroxyphenyl)-2-(iodoamino)propanamide Chemical compound NC(=O)[C@@H](NI)CC1=CC=C(O)C=C1 NGCVFIUAYANGKF-QMMMGPOBSA-N 0.000 claims description 2
- 239000004475 Arginine Chemical group 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical group C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical group NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Chemical group OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 108010075130 AAP 10 Proteins 0.000 description 15
- 230000001536 pro-arrhythmogenic effect Effects 0.000 description 13
- 230000036982 action potential Effects 0.000 description 9
- 206010003119 arrhythmia Diseases 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 230000006793 arrhythmia Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 230000003531 anti-dysrhythmic effect Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 150000003053 piperidines Chemical class 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 206010003497 Asphyxia Diseases 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- DJBNUMBKLMJRSA-UHFFFAOYSA-N Flecainide Chemical compound FC(F)(F)COC1=CC=C(OCC(F)(F)F)C(C(=O)NCC2NCCCC2)=C1 DJBNUMBKLMJRSA-UHFFFAOYSA-N 0.000 description 3
- 102000004310 Ion Channels Human genes 0.000 description 3
- 108090000862 Ion Channels Proteins 0.000 description 3
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229960000449 flecainide Drugs 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 229960004194 lidocaine Drugs 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- -1 methoxycarbonyl (fluorenylmethoxycarbonyl)-iodotyrosine Chemical compound 0.000 description 2
- ZLVYMPOQNJTFSG-QMMMGPOBSA-N monoiodotyrosine Chemical compound OC(=O)[C@@H](NI)CC1=CC=C(O)C=C1 ZLVYMPOQNJTFSG-QMMMGPOBSA-N 0.000 description 2
- 210000003516 pericardium Anatomy 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- QWXZOFZKSQXPDC-NSHDSACASA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)propanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](C)C(O)=O)C3=CC=CC=C3C2=C1 QWXZOFZKSQXPDC-NSHDSACASA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 108090000312 Calcium Channels Proteins 0.000 description 1
- 102000003922 Calcium Channels Human genes 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102000004257 Potassium Channel Human genes 0.000 description 1
- 108010052164 Sodium Channels Proteins 0.000 description 1
- 102000018674 Sodium Channels Human genes 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 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
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 108020001213 potassium channel Proteins 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011894 semi-preparative HPLC Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Cardiology (AREA)
- Biophysics (AREA)
- Heart & Thoracic Surgery (AREA)
- Biochemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19500990.8 | 1995-01-14 | ||
DE19500990A DE19500990A1 (de) | 1995-01-14 | 1995-01-14 | Neues Peptid, seine Herstellung und Verwendung |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1168142A true CN1168142A (zh) | 1997-12-17 |
Family
ID=7751510
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN96191447A Pending CN1168142A (zh) | 1995-01-14 | 1996-01-04 | 新肽及其制备方法和用途 |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP0805818A1 (no) |
JP (1) | JPH11511727A (no) |
KR (1) | KR19980701397A (no) |
CN (1) | CN1168142A (no) |
AU (1) | AU4483696A (no) |
BR (1) | BR9606756A (no) |
CA (1) | CA2209496A1 (no) |
CZ (1) | CZ204897A3 (no) |
DE (1) | DE19500990A1 (no) |
FI (1) | FI972965A0 (no) |
IL (1) | IL116658A0 (no) |
NO (1) | NO973230L (no) |
WO (1) | WO1996021674A1 (no) |
ZA (1) | ZA96239B (no) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111303249A (zh) * | 2020-01-02 | 2020-06-19 | 兰州大学 | 一种特异性检测病变胶原蛋白的探针、制备方法及应用 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7585839B2 (en) | 2000-02-23 | 2009-09-08 | Zealand Pharma A/S | Medical uses of intercellular communication facilitating compounds |
ES2228807T3 (es) * | 2000-02-23 | 2005-04-16 | Zealand Pharma A/S | Nuevo peptidos antiarritmicos. |
US7250397B2 (en) | 2000-02-23 | 2007-07-31 | Zealand Pharma A/S | Antiarrhythmic peptides |
JP2005506295A (ja) * | 2001-02-22 | 2005-03-03 | ジーランド ファーマ アクティーゼルスカブ | 細胞間連絡促進化合物の新規医薬使用 |
EA007792B1 (ru) * | 2001-02-22 | 2007-02-27 | Зеаланд Фарма А/С | Новое медицинское применение соединений, способствующих межклеточным связям |
EA006860B1 (ru) * | 2002-01-29 | 2006-04-28 | Уайт | Композиции и способы модулирования гемиканалов коннексина |
-
1995
- 1995-01-14 DE DE19500990A patent/DE19500990A1/de not_active Withdrawn
-
1996
- 1996-01-02 IL IL11665896A patent/IL116658A0/xx unknown
- 1996-01-04 KR KR1019970704786A patent/KR19980701397A/ko not_active Application Discontinuation
- 1996-01-04 JP JP8521413A patent/JPH11511727A/ja active Pending
- 1996-01-04 CZ CZ972048A patent/CZ204897A3/cs unknown
- 1996-01-04 EP EP96900898A patent/EP0805818A1/de not_active Withdrawn
- 1996-01-04 AU AU44836/96A patent/AU4483696A/en not_active Abandoned
- 1996-01-04 WO PCT/EP1996/000009 patent/WO1996021674A1/de not_active Application Discontinuation
- 1996-01-04 CA CA002209496A patent/CA2209496A1/en not_active Abandoned
- 1996-01-04 CN CN96191447A patent/CN1168142A/zh active Pending
- 1996-01-04 BR BR9606756A patent/BR9606756A/pt not_active Application Discontinuation
- 1996-01-12 ZA ZA96239A patent/ZA96239B/xx unknown
-
1997
- 1997-07-11 FI FI972965A patent/FI972965A0/fi unknown
- 1997-07-11 NO NO973230A patent/NO973230L/no unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111303249A (zh) * | 2020-01-02 | 2020-06-19 | 兰州大学 | 一种特异性检测病变胶原蛋白的探针、制备方法及应用 |
Also Published As
Publication number | Publication date |
---|---|
EP0805818A1 (de) | 1997-11-12 |
IL116658A0 (en) | 1996-05-14 |
AU4483696A (en) | 1996-07-31 |
WO1996021674A1 (de) | 1996-07-18 |
KR19980701397A (ko) | 1998-05-15 |
JPH11511727A (ja) | 1999-10-12 |
ZA96239B (en) | 1997-07-14 |
FI972965A (fi) | 1997-07-11 |
BR9606756A (pt) | 1998-01-06 |
CZ204897A3 (en) | 1997-12-17 |
DE19500990A1 (de) | 1996-07-18 |
NO973230D0 (no) | 1997-07-11 |
CA2209496A1 (en) | 1996-07-18 |
FI972965A0 (fi) | 1997-07-11 |
MX9704796A (es) | 1997-10-31 |
NO973230L (no) | 1997-07-11 |
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Legal Events
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---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C01 | Deemed withdrawal of patent application (patent law 1993) | ||
WD01 | Invention patent application deemed withdrawn after publication |