DE69838331T2 - Kollagenähnliche verbindungen - Google Patents
Kollagenähnliche verbindungen Download PDFInfo
- Publication number
- DE69838331T2 DE69838331T2 DE69838331T DE69838331T DE69838331T2 DE 69838331 T2 DE69838331 T2 DE 69838331T2 DE 69838331 T DE69838331 T DE 69838331T DE 69838331 T DE69838331 T DE 69838331T DE 69838331 T2 DE69838331 T2 DE 69838331T2
- Authority
- DE
- Germany
- Prior art keywords
- collagen
- flp
- stability
- xaa
- triple helix
- 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 description 21
- 102000008186 Collagen Human genes 0.000 title abstract description 98
- 108010035532 Collagen Proteins 0.000 title abstract description 98
- 229920001436 collagen Polymers 0.000 title abstract description 98
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 20
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 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 4
- KZMRGTASBWZPFC-SCSAIBSYSA-N (2r)-1-fluoropyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCN1F KZMRGTASBWZPFC-SCSAIBSYSA-N 0.000 claims description 3
- 125000000539 amino acid group Chemical group 0.000 claims 2
- LEIKGVHQTKHOLM-IUCAKERBSA-N Pro-Pro-Gly Chemical compound OC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@H]1NCCC1 LEIKGVHQTKHOLM-IUCAKERBSA-N 0.000 abstract description 13
- 108010087846 prolyl-prolyl-glycine Proteins 0.000 abstract description 13
- 229960002429 proline Drugs 0.000 abstract description 10
- 230000003278 mimic effect Effects 0.000 abstract description 3
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical group O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 230000001939 inductive effect Effects 0.000 description 12
- 102000004196 processed proteins & peptides Human genes 0.000 description 11
- 210000001519 tissue Anatomy 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- BZSXSIQTILQTNQ-SCWOKBSMSA-N (prolyl-hydroxylprolyl-glycine)10 Chemical group N1([C@@H](C[C@H](C1)O)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)NCC(O)=O)C(=O)C1CCCN1 BZSXSIQTILQTNQ-SCWOKBSMSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 230000018109 developmental process Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 102000004169 proteins and genes Human genes 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- 229940024606 amino acid Drugs 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 229920001184 polypeptide Polymers 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 230000029663 wound healing Effects 0.000 description 6
- 238000007385 chemical modification Methods 0.000 description 5
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 229960002591 hydroxyproline Drugs 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 229910000679 solder Inorganic materials 0.000 description 5
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 5
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 4
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 4
- 206010052428 Wound Diseases 0.000 description 4
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 238000002983 circular dichroism Methods 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
- 238000013461 design Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000003466 welding Methods 0.000 description 4
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- -1 Boc group Chemical group 0.000 description 3
- 229920001222 biopolymer Polymers 0.000 description 3
- 210000000988 bone and bone Anatomy 0.000 description 3
- 210000000845 cartilage Anatomy 0.000 description 3
- 238000001142 circular dichroism spectrum Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 210000002435 tendon Anatomy 0.000 description 3
- 125000003508 trans-4-hydroxy-L-proline group Chemical group 0.000 description 3
- KZMRGTASBWZPFC-BYPYZUCNSA-N (2s)-1-fluoropyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1F KZMRGTASBWZPFC-BYPYZUCNSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 230000033444 hydroxylation Effects 0.000 description 2
- 238000005805 hydroxylation reaction Methods 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ZQEBQGAAWMOMAI-ZETCQYMHSA-N (2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C(O)=O ZQEBQGAAWMOMAI-ZETCQYMHSA-N 0.000 description 1
- ZPBIYZHGBPBZCK-VKHMYHEASA-N (2s)-4,4-difluoropyrrolidin-1-ium-2-carboxylate Chemical compound OC(=O)[C@@H]1CC(F)(F)CN1 ZPBIYZHGBPBZCK-VKHMYHEASA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 108020004705 Codon Proteins 0.000 description 1
- 208000027932 Collagen disease Diseases 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- MVORZMQFXBLMHM-QWRGUYRKSA-N Gly-His-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](NC(=O)CN)CC1=CN=CN1 MVORZMQFXBLMHM-QWRGUYRKSA-N 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102000007079 Peptide Fragments Human genes 0.000 description 1
- 108010033276 Peptide Fragments Proteins 0.000 description 1
- 101710172711 Structural protein Proteins 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000036570 collagen biosynthesis Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000009144 enzymatic modification Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002163 immunogen Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- WCIXKWOJEMZXMK-ZETCQYMHSA-N methyl (2s)-1-acetylpyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1CCCN1C(C)=O WCIXKWOJEMZXMK-ZETCQYMHSA-N 0.000 description 1
- RRXCEVZGPPDCGR-RQJHMYQMSA-N methyl (2s,4r)-1-acetyl-4-hydroxypyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1C[C@@H](O)CN1C(C)=O RRXCEVZGPPDCGR-RQJHMYQMSA-N 0.000 description 1
- 238000000302 molecular modelling Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000004153 renaturation Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000000515 tooth Anatomy 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
Classifications
-
- 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
- C07K14/78—Connective tissue peptides, e.g. collagen, elastin, laminin, fibronectin, vitronectin or cold insoluble globulin [CIG]
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Toxicology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US918223 | 1978-06-23 | ||
| US08/918,223 US5973112A (en) | 1997-08-25 | 1997-08-25 | Collagen mimics |
| PCT/US1998/014284 WO1999010381A1 (en) | 1997-08-25 | 1998-07-09 | Collagen mimics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69838331D1 DE69838331D1 (de) | 2007-10-11 |
| DE69838331T2 true DE69838331T2 (de) | 2008-05-21 |
Family
ID=25440014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69838331T Expired - Lifetime DE69838331T2 (de) | 1997-08-25 | 1998-07-09 | Kollagenähnliche verbindungen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5973112A (https=) |
| EP (1) | EP1007568B1 (https=) |
| JP (1) | JP4514328B2 (https=) |
| AT (1) | ATE371672T1 (https=) |
| AU (1) | AU8480698A (https=) |
| CA (1) | CA2301175C (https=) |
| DE (1) | DE69838331T2 (https=) |
| WO (1) | WO1999010381A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2452593C (en) * | 2001-07-12 | 2015-02-03 | Arexis Ab | Triple polypeptide complexes |
| JP5070442B2 (ja) * | 2002-02-28 | 2012-11-14 | 株式会社Ｐｈｇ | 新規なポリペプチドおよびその製造方法 |
| WO2005000872A2 (en) * | 2003-06-23 | 2005-01-06 | Wisconsin Alumni Research Foundation | Collagen mimics |
| WO2005078085A1 (ja) * | 2004-02-16 | 2005-08-25 | Techno Network Shikoku Co., Ltd. | コラーゲン様構造を有するポリペプチド |
| JP5601437B2 (ja) * | 2004-02-16 | 2014-10-08 | 株式会社テクノネットワーク四国 | コラーゲン様構造を有するポリペプチド |
| US9758569B2 (en) * | 2006-05-26 | 2017-09-12 | Wisconsin Alumni Research Foundation | Collagen mimics |
| CN101072380B (zh) * | 2007-06-08 | 2010-12-08 | 华为技术有限公司 | 内容下发方法及系统、网络设备、移动数据业务管理平台 |
| US20090299034A1 (en) * | 2007-08-01 | 2009-12-03 | Mabel Alamino Cejas | Collagen-related peptides |
| CA2695288A1 (en) | 2007-08-01 | 2009-02-05 | Ethicon, Inc. | Collagen-related peptides and uses thereof |
| US7858741B2 (en) * | 2008-02-06 | 2010-12-28 | Wisconsin Alumni Research Foundation | Stabilization of the collagen triple helix by O-methylation of hydroxyproline residues |
| US20100021527A1 (en) * | 2008-07-25 | 2010-01-28 | Chunlin Yang | Collagen-related peptides and uses thereof and hemostatic foam substrates |
| BR112019021056B1 (pt) | 2017-04-06 | 2022-11-22 | Sustain Holdings, Llc | Usos de uma composição que compreende um peptídeo mimético de colágeno para o tratamento ou a prevenção de uma doença, distúrbio ou ferida ocular |
| EP3958889B1 (en) | 2019-04-22 | 2025-01-08 | Sustain Holdings, LLC | Collagen mimetic peptide compositions for treating a posterior segment ocular disease or disorder involving the retina, retinal blood vessels, retinal nerves or optic nerve |
| CN117903293B (zh) * | 2024-03-19 | 2025-01-07 | 如凤凰再生科技发展(成都)有限公司 | 一种具有热稳定性和促进自身胶原生成的三螺旋胶原蛋白及其制备方法和用途 |
| CN119019539B (zh) * | 2024-09-04 | 2025-07-18 | 上海欣肽生物科技有限公司 | 一种长链类胶原蛋白多肽的迭代指数合成方法 |
-
1997
- 1997-08-25 US US08/918,223 patent/US5973112A/en not_active Expired - Lifetime
-
1998
- 1998-07-09 JP JP2000507706A patent/JP4514328B2/ja not_active Expired - Lifetime
- 1998-07-09 CA CA2301175A patent/CA2301175C/en not_active Expired - Lifetime
- 1998-07-09 AT AT98935594T patent/ATE371672T1/de not_active IP Right Cessation
- 1998-07-09 EP EP98935594A patent/EP1007568B1/en not_active Expired - Lifetime
- 1998-07-09 DE DE69838331T patent/DE69838331T2/de not_active Expired - Lifetime
- 1998-07-09 AU AU84806/98A patent/AU8480698A/en not_active Abandoned
- 1998-07-09 WO PCT/US1998/014284 patent/WO1999010381A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1007568B1 (en) | 2007-08-29 |
| CA2301175C (en) | 2010-01-26 |
| EP1007568A1 (en) | 2000-06-14 |
| ATE371672T1 (de) | 2007-09-15 |
| DE69838331D1 (de) | 2007-10-11 |
| WO1999010381A1 (en) | 1999-03-04 |
| US5973112A (en) | 1999-10-26 |
| CA2301175A1 (en) | 1999-03-04 |
| JP2001514189A (ja) | 2001-09-11 |
| JP4514328B2 (ja) | 2010-07-28 |
| AU8480698A (en) | 1999-03-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69838331T2 (de) | Kollagenähnliche verbindungen | |
| DE3588120T2 (de) | Kollagenknochenersatzmaterial | |
| DE3789507T2 (de) | Temperaturabhängige kraft- und strukturentwicklung von elastin polytetrapeptiden und polypentapeptiden. | |
| DE68917300T2 (de) | Heilung von wunden. | |
| DE60012721T2 (de) | Analoge des magensaft inhibierenden peptides und ihre verwendung für die behandlung von diabetes | |
| JP3101739B2 (ja) | 天然の骨組織から骨形成術のための材料を製造する方法及びこれによって得られた材料 | |
| DE69020466T2 (de) | Collagen-Zubereitungen und Verfahren zur Herstellung davon. | |
| DE3752364T2 (de) | Osteoinduktive Zusammensetzungen | |
| DE60021388T2 (de) | Monomeres protein der tgf-beta familie | |
| DE60015082T2 (de) | Künstliche peptide mit oberflächenaktivität und ihre verwendung zur herstellung von künstlichen tensiden | |
| DE69129865T2 (de) | Osteogene peptide | |
| DE69525177T2 (de) | Neurotrophe peptide des aktivitätsabhängigen neurotrophen faktors | |
| DE3586616T2 (de) | Verfahren zur verhuetung und induktion menschlicher plaettchen-aggregation. | |
| DE69219590T2 (de) | BPC-Peptide, deren Herstellung und Verwendung | |
| DE2647843A1 (de) | Neue peptide, ihre herstellung sowie verfahren zur herstellung cyclischer peptide | |
| DE69133338T2 (de) | Bmp-5-derivate | |
| DE69332654T2 (de) | Fragmente eines oberflächenaktiven lungenproteins | |
| DE69426569T2 (de) | Bivalente thrombininhibitore | |
| WO2004020470A1 (ja) | システインプロテアーゼ処理コラーゲンの製造方法およびシステインプロテアーゼ処理コラーゲン | |
| DE69020755T3 (de) | Physiologisch aktives Polypeptid und DNA. | |
| DE69133087T2 (de) | Kombination aus IGF-I und TGF-beta zur Knochenregenerierung | |
| DE3937076A1 (de) | Kollagene, verfahren zu ihrer herstellung und kosmetische mittel | |
| EP1709064B1 (de) | Dna-sequenz und rekombinante herstellung des graspollen-allergens lol p 4 | |
| DE3750223T2 (de) | Segmentierte polypeptid-bioelastomere zur modulierung des elastizitaetsmoduls. | |
| DE2462222A1 (de) | Loesliches, natives human-kollagen, dessen nicht-helikale peptide teilweise oder vollstaendig abgetrennt sind |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |