JP4346650B2 - メタスチン誘導体およびその用途 - Google Patents
メタスチン誘導体およびその用途 Download PDFInfo
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- JP4346650B2 JP4346650B2 JP2006554374A JP2006554374A JP4346650B2 JP 4346650 B2 JP4346650 B2 JP 4346650B2 JP 2006554374 A JP2006554374 A JP 2006554374A JP 2006554374 A JP2006554374 A JP 2006554374A JP 4346650 B2 JP4346650 B2 JP 4346650B2
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- Prior art keywords
- arg
- trp
- asn
- phe
- compound
- Prior art date
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- KAHDONZOCXSKII-NJVVDGNHSA-N kisspeptin Chemical class C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H]1N(CCC1)C(=O)[C@H]1N(CCC1)C(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)O)C1=CN=CN1 KAHDONZOCXSKII-NJVVDGNHSA-N 0.000 title description 124
- 150000001875 compounds Chemical class 0.000 claims description 1125
- 150000003839 salts Chemical class 0.000 claims description 83
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 753
- -1 glyoxyloyl group Chemical group 0.000 description 712
- VEVRNHHLCPGNDU-MUGJNUQGSA-O desmosine Chemical compound OC(=O)[C@@H](N)CCCC[N+]1=CC(CC[C@H](N)C(O)=O)=C(CCC[C@H](N)C(O)=O)C(CC[C@H](N)C(O)=O)=C1 VEVRNHHLCPGNDU-MUGJNUQGSA-O 0.000 description 614
- OUYCCCASQSFEME-MRVPVSSYSA-N D-tyrosine Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-MRVPVSSYSA-N 0.000 description 98
- 125000001424 substituent group Chemical group 0.000 description 94
- 235000002639 sodium chloride Nutrition 0.000 description 90
- 125000004432 carbon atom Chemical group C* 0.000 description 86
- 239000003814 drug Substances 0.000 description 85
- 125000003118 aryl group Chemical group 0.000 description 75
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 74
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 70
- 125000005842 heteroatom Chemical group 0.000 description 69
- 229910052717 sulfur Inorganic materials 0.000 description 69
- 229910052757 nitrogen Inorganic materials 0.000 description 68
- 125000000217 alkyl group Chemical group 0.000 description 61
- 125000004430 oxygen atom Chemical group O* 0.000 description 60
- 125000004434 sulfur atom Chemical group 0.000 description 58
- 125000004433 nitrogen atom Chemical group N* 0.000 description 57
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 54
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 description 53
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 43
- RTFXPCYMDYBZNQ-SRVKXCTJSA-N Asn-Tyr-Asn Chemical compound [H]N[C@@H](CC(N)=O)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N[C@@H](CC(N)=O)C(O)=O RTFXPCYMDYBZNQ-SRVKXCTJSA-N 0.000 description 38
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 38
- IVPNEDNYYYFAGI-GARJFASQSA-N Asp-Leu-Pro Chemical compound CC(C)C[C@@H](C(=O)N1CCC[C@@H]1C(=O)O)NC(=O)[C@H](CC(=O)O)N IVPNEDNYYYFAGI-GARJFASQSA-N 0.000 description 37
- 238000000034 method Methods 0.000 description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 37
- OGUPCHKBOKJFMA-SRVKXCTJSA-N Arg-Glu-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](N)CCCN=C(N)N OGUPCHKBOKJFMA-SRVKXCTJSA-N 0.000 description 36
- 108010003700 lysyl aspartic acid Proteins 0.000 description 36
- MVJRBCJCRYGCKV-GVXVVHGQSA-N Leu-Val-Gln Chemical compound [H]N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O MVJRBCJCRYGCKV-GVXVVHGQSA-N 0.000 description 35
- 230000028327 secretion Effects 0.000 description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 28
- 125000000623 heterocyclic group Chemical group 0.000 description 27
- 206010028980 Neoplasm Diseases 0.000 description 26
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 26
- 108090000765 processed proteins & peptides Proteins 0.000 description 24
- 229940124597 therapeutic agent Drugs 0.000 description 24
- 101150002976 ACP1 gene Proteins 0.000 description 23
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 23
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 22
- 229910052799 carbon Inorganic materials 0.000 description 22
- 239000003163 gonadal steroid hormone Substances 0.000 description 21
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- 108010086677 Gonadotropins Proteins 0.000 description 20
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- 238000002360 preparation method Methods 0.000 description 20
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
- 241000124008 Mammalia Species 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 125000002252 acyl group Chemical group 0.000 description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 18
- 125000006239 protecting group Chemical group 0.000 description 18
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 17
- 125000003275 alpha amino acid group Chemical group 0.000 description 17
- 230000002401 inhibitory effect Effects 0.000 description 17
- 229910052760 oxygen Inorganic materials 0.000 description 17
- 230000000069 prophylactic effect Effects 0.000 description 17
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 16
- 108010087924 alanylproline Proteins 0.000 description 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 15
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 15
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 15
- 102000013599 Kisspeptins Human genes 0.000 description 15
- 108010012048 Kisspeptins Proteins 0.000 description 15
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 15
- 125000003277 amino group Chemical group 0.000 description 15
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 14
- 125000004122 cyclic group Chemical group 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 13
- QWZIOCFPXMAXET-CIUDSAMLSA-N Ser-Arg-Gln Chemical compound [H]N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(O)=O QWZIOCFPXMAXET-CIUDSAMLSA-N 0.000 description 13
- 125000003710 aryl alkyl group Chemical group 0.000 description 13
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 13
- 229940088597 hormone Drugs 0.000 description 13
- 239000005556 hormone Substances 0.000 description 13
- 125000001544 thienyl group Chemical group 0.000 description 13
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- PMGDADKJMCOXHX-UHFFFAOYSA-N L-Arginyl-L-glutamin-acetat Natural products NC(=N)NCCCC(N)C(=O)NC(CCC(N)=O)C(O)=O PMGDADKJMCOXHX-UHFFFAOYSA-N 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 12
- 108010008355 arginyl-glutamine Proteins 0.000 description 12
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229910052698 phosphorus Inorganic materials 0.000 description 12
- 230000001737 promoting effect Effects 0.000 description 12
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 11
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 11
- VSXBYIJUAXPAAL-WDSKDSINSA-N Gln-Gly-Ala Chemical compound OC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](N)CCC(N)=O VSXBYIJUAXPAAL-WDSKDSINSA-N 0.000 description 11
- JRDYDYXZKFNNRQ-XPUUQOCRSA-N Gly-Ala-Val Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)CN JRDYDYXZKFNNRQ-XPUUQOCRSA-N 0.000 description 11
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 11
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- FEGOCLZUJUFCHP-CIUDSAMLSA-N Ala-Pro-Gln Chemical compound [H]N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(O)=O FEGOCLZUJUFCHP-CIUDSAMLSA-N 0.000 description 10
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- 125000002102 aryl alkyloxo group Chemical group 0.000 description 7
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- 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 7
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- Health & Medical Sciences (AREA)
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Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE385193T1 (de) | 2002-03-20 | 2008-02-15 | Mannkind Corp | Inhalationsgerät |
| KR20050090420A (ko) | 2002-12-26 | 2005-09-13 | 다케다 야쿠힌 고교 가부시키가이샤 | 메타스틴 유도체 및 이의 용도 |
| CA2518541C (en) | 2003-03-12 | 2013-05-21 | Takeda Pharmaceutical Company Limited | Gonadal function improving agents |
| CN101035620B (zh) | 2004-04-08 | 2012-01-04 | 生物马特里卡公司 | 用于生命科学的样品存储和样品管理的综合 |
| WO2006001499A2 (en) * | 2004-06-25 | 2006-01-05 | Takeda Pharmaceutical Company Limited | Metastin derivatives and use thereof |
| DK1786784T3 (da) | 2004-08-20 | 2011-02-14 | Mannkind Corp | Katalyse af diketopiperazinsyntese |
| BRPI0514293B1 (pt) | 2004-08-23 | 2022-07-19 | Mannkind Corporation | Sistema microparticulado para distribuição de droga |
| DK1928423T3 (en) | 2005-09-14 | 2016-02-29 | Mannkind Corp | A method for drug formulation based on increasing the affinity of the active substances to the crystalline microparticle surfaces |
| TWI386417B (zh) | 2005-12-22 | 2013-02-21 | Takeda Pharmaceutical | 轉移抑素衍生物及其用途 |
| US8404643B2 (en) | 2005-12-22 | 2013-03-26 | Takeda Pharmaceutical Company Limited | Metastin derivatives and use thereof |
| US20090093615A1 (en) * | 2005-12-22 | 2009-04-09 | Takeda Pharmaceutical Company Limited | Metastin derivatives and use thereof |
| CA2643464C (en) | 2006-02-22 | 2018-09-04 | Mannkind Corporation | A method for improving the pharmaceutic properties of microparticles comprising diketopiperazine and an active agent |
| US8183212B2 (en) * | 2006-04-26 | 2012-05-22 | Kyoto University | Compound having GPR54 agonistic activity |
| ITMI20061607A1 (it) | 2006-08-09 | 2008-02-10 | Maria Vincenza Carriero | Peptidi con attivita farmacologica |
| JO3048B1 (ar) | 2006-10-25 | 2016-09-05 | Takeda Pharmaceuticals Co | مشتقات متاستين واستخدامها |
| CN101528772B (zh) * | 2006-10-25 | 2013-03-13 | 武田药品工业株式会社 | Metastin衍生物及其用途 |
| WO2011163272A1 (en) | 2010-06-21 | 2011-12-29 | Mannkind Corporation | Dry powder drug delivery system and methods |
| EP2277900A4 (en) | 2008-04-24 | 2011-08-03 | Takeda Pharmaceutical | METASTINE DERIVATIVE AND ITS USE |
| US8592379B2 (en) | 2008-04-30 | 2013-11-26 | Kyoto University | Metastin derivative and use thereof |
| US8485180B2 (en) | 2008-06-13 | 2013-07-16 | Mannkind Corporation | Dry powder drug delivery system |
| CN106039494B (zh) | 2008-06-13 | 2019-12-24 | 曼金德公司 | 干粉吸入器和用于药物输送的系统 |
| BRPI0914308B8 (pt) | 2008-06-20 | 2021-06-22 | Mannkind Corp | sistema de inalação |
| JP5698977B2 (ja) | 2008-07-30 | 2015-04-08 | 武田薬品工業株式会社 | メタスチン誘導体およびその用途 |
| UY32367A (es) * | 2008-12-29 | 2010-07-30 | Takeda Pharmaceutical | Agente preventivo/terapéutico contra el cáncer |
| US8314106B2 (en) | 2008-12-29 | 2012-11-20 | Mannkind Corporation | Substituted diketopiperazine analogs for use as drug delivery agents |
| WO2010137022A1 (en) | 2009-05-27 | 2010-12-02 | Yeda Research And Development Co. Ltd | Gpr54 agonists or antagonists for treatment of diseases presenting behavioral abnormalities |
| MA33910B1 (fr) | 2009-12-22 | 2013-01-02 | Takeda Pharmaceutcal Company Ltd | Formulation à libération prolongée |
| CA2806734A1 (en) | 2010-07-26 | 2012-02-09 | Biomatrica, Inc. | Compositions for stabilizing dna, rna and proteins in saliva and other biological samples during shipping and storage at ambient temperatures |
| EP2598660B1 (en) | 2010-07-26 | 2017-03-15 | Biomatrica, INC. | Compositions for stabilizing dna, rna and proteins in blood and other biological samples during shipping and storage at ambient temperatures |
| MY180552A (en) | 2011-04-01 | 2020-12-02 | Mannkind Corp | Blister package for pharmaceutical cartridges |
| WO2012174472A1 (en) | 2011-06-17 | 2012-12-20 | Mannkind Corporation | High capacity diketopiperazine microparticles |
| EP2755690B1 (en) | 2011-08-04 | 2020-04-01 | Merck Sharp & Dohme B.V. | Kisspeptide-pentasaccharide conjugates |
| JP6018640B2 (ja) * | 2011-10-24 | 2016-11-02 | マンカインド コーポレイション | 疼痛を緩和するのに有効な鎮痛組成物並びに当該組成物を含む乾燥粉末及び乾燥粉末薬剤輸送システム |
| CN104350064A (zh) | 2012-03-14 | 2015-02-11 | 耶达研究及发展有限公司 | 修饰的吻素肽和其用途 |
| DK2872205T3 (en) | 2012-07-12 | 2017-02-27 | Mannkind Corp | DRY POWDER FORMAL ADMINISTRATION SYSTEM |
| EP2934572A4 (en) | 2012-12-20 | 2016-11-23 | Biomatrica Inc | FORMULATIONS AND METHODS FOR STABILIZING PCR REAGENTS |
| JP6143270B2 (ja) * | 2013-01-31 | 2017-06-07 | 学校法人東京薬科大学 | マイオスタチン阻害ペプチド |
| EP3021834A1 (en) | 2013-07-18 | 2016-05-25 | MannKind Corporation | Heat-stable dry powder pharmaceutical compositions and methods |
| WO2015112703A1 (en) * | 2014-01-22 | 2015-07-30 | The Johns Hopkins University | Compositions and methods for treating diabetes |
| WO2015148905A1 (en) | 2014-03-28 | 2015-10-01 | Mannkind Corporation | Use of ultrarapid acting insulin |
| CN113826612B (zh) | 2014-06-10 | 2022-11-22 | 生物马特里卡公司 | 在环境温度下稳定凝血细胞 |
| BR112018011639A2 (pt) | 2015-12-08 | 2018-11-27 | Biomatrica Inc | redução de taxa de sedimentação de eritrócitos |
| IL311335A (en) | 2016-09-30 | 2024-05-01 | Sumitomo Pharma Switzerland Gmbh | Methods for treating female infertility |
| WO2019007383A1 (zh) | 2017-07-05 | 2019-01-10 | 凯惠科技发展(上海)有限公司 | 一种肽类化合物、其应用及含其的组合物 |
| CN108752233B (zh) * | 2018-07-18 | 2020-10-16 | 河北师范大学 | 小分子凝胶因子、凝胶材料及制备方法和应用 |
| EP4146629A4 (en) * | 2020-05-08 | 2024-10-23 | The Feinstein Institutes for Medical Research | Dimers for use in synthesis of peptidomimetics |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1524747A (en) * | 1976-05-11 | 1978-09-13 | Ici Ltd | Polypeptide |
| FR2488253A1 (fr) * | 1980-08-08 | 1982-02-12 | Roques Bernard | Nouveaux peptides et leur application en therapeutique |
| IL74827A (en) | 1984-05-21 | 1989-06-30 | Salk Inst For Biological Studi | Peptides active as gnrh antagonists and pharmaceutical compositions containing them |
| MX9100717A (es) * | 1990-08-24 | 1992-04-01 | Syntex Inc | Antagonistas de la bradiquinina |
| US5824784A (en) | 1994-10-12 | 1998-10-20 | Amgen Inc. | N-terminally chemically modified protein compositions and methods |
| JPH09169735A (ja) | 1995-10-19 | 1997-06-30 | Takeda Chem Ind Ltd | キノリン誘導体、その製造法および用途 |
| AU7333496A (en) | 1995-10-19 | 1997-05-07 | Takeda Chemical Industries Ltd. | Quinoline derivatives as gnrh antagonists |
| JP2000510453A (ja) | 1996-04-19 | 2000-08-15 | ノボ ノルディスク アクティーゼルスカブ | 成長ホルモン遊離特性を有する化合物 |
| CA2283299A1 (en) | 1997-03-07 | 1998-09-11 | Human Genome Sciences, Inc. | 186 human secreted proteins |
| JP4486187B2 (ja) | 1998-10-27 | 2010-06-23 | 武田薬品工業株式会社 | 新規ｇ蛋白質共役型レセプター蛋白質、そのｄｎａおよびそのリガンド |
| US6528054B1 (en) | 1998-12-28 | 2003-03-04 | Corixa Corporation | Compositions and methods for the therapy and diagnosis of breast cancer |
| WO2001000228A1 (de) | 1999-06-28 | 2001-01-04 | Basf Aktiengesellschaft | Verfahren zur verhinderung von tumorwachstum |
| US6638906B1 (en) | 1999-12-13 | 2003-10-28 | Nobex Corporation | Amphiphilic polymers and polypeptide conjugates comprising same |
| AU1889101A (en) | 1999-12-17 | 2001-06-25 | Takeda Chemical Industries Ltd. | Process for producing kiss-1 peptide |
| JP2001231581A (ja) * | 1999-12-17 | 2001-08-28 | Takeda Chem Ind Ltd | ＫｉＳＳ−１ペプチドの製造法 |
| CZ20023567A3 (cs) | 2000-03-29 | 2003-11-12 | Corixa Corporation | Sloučeniny a způsoby pro terapii a diagnostiku karcinomu plic |
| EP1273658A4 (en) | 2000-03-30 | 2004-08-11 | Takeda Chemical Industries Ltd | NEW PROTEIN, THEIR DNA AND METHOD FOR THE PRODUCTION THEREOF |
| US7834141B1 (en) | 2000-03-31 | 2010-11-16 | Theresa Siler-Khodr | Non-mammalian GnRH analogs and uses thereof in tumor cell growth regulation and cancer therapy |
| RU2311920C2 (ru) | 2000-09-20 | 2007-12-10 | Корикса Корпорейшн | Композиции и способы для лечения и диагностики рака легких |
| JP2003026601A (ja) | 2000-11-29 | 2003-01-29 | Takeda Chem Ind Ltd | 医薬組成物およびその製造法 |
| JP2002320496A (ja) | 2001-02-26 | 2002-11-05 | Takeda Chem Ind Ltd | 新規マウス型ＫｉＳＳ−１レセプタータンパク質およびそのＤＮＡ |
| WO2002085399A1 (fr) | 2001-04-20 | 2002-10-31 | Takeda Chemical Industries, Ltd. | Preparations contenant un peptide |
| CN1509336A (zh) | 2001-05-17 | 2004-06-30 | 株式会社岛津制作所 | 肽的制备方法 |
| ATE360034T1 (de) | 2001-09-19 | 2007-05-15 | Takeda Pharmaceutical | Antikörper gegen metastin und dessen verwendung zur diagnose von schwangerschaft |
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| JP2003300906A (ja) | 2002-04-12 | 2003-10-21 | Daiichi Fine Chemical Co Ltd | がん転移抑制因子の安定化 |
| JPWO2004035089A1 (ja) | 2002-10-09 | 2006-02-09 | 協和醗酵工業株式会社 | ホルモン依存性癌の治療剤 |
| MXPA05004380A (es) | 2002-10-25 | 2005-11-23 | Paradigm Therapeutics Ltd | Mamiferos gpr54 knock out y metodos de investigacion que los utilizan. |
| JP4804714B2 (ja) | 2002-12-26 | 2011-11-02 | 武田薬品工業株式会社 | メタスチン誘導体およびその用途 |
| KR20050090420A (ko) | 2002-12-26 | 2005-09-13 | 다케다 야쿠힌 고교 가부시키가이샤 | 메타스틴 유도체 및 이의 용도 |
| US6800611B2 (en) * | 2003-01-06 | 2004-10-05 | Takeda Chemical Industries, Ltd. | Metastin derivatives and their use |
| KR100595364B1 (ko) | 2003-02-20 | 2006-07-03 | 재단법인 목암생명공학연구소 | Ｌｋ8 단백질을 유효성분으로 포함하는 항암제 |
| CA2518541C (en) | 2003-03-12 | 2013-05-21 | Takeda Pharmaceutical Company Limited | Gonadal function improving agents |
| EP1464652A1 (en) | 2003-04-02 | 2004-10-06 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | GPR54 receptor agonist and antagonist useful for the treatment of gonadotropin related diseases |
| US20050002935A1 (en) | 2003-04-17 | 2005-01-06 | Vincent Ling | Use of B7-H3 as an immunoregulatory agent |
| US20050026224A1 (en) | 2003-04-28 | 2005-02-03 | Follettie Maximillian T. | Methods and compositions for modulating G-protein coupled receptor 54 |
| WO2004101747A2 (en) | 2003-05-07 | 2004-11-25 | The General Hospital Corporation | Identification and use of gpr54 and its ligands for reproductive disorders and contraception |
| WO2004106289A1 (en) | 2003-05-30 | 2004-12-09 | Prozymex A/S | Protease inhibitors |
| RU2333221C2 (ru) | 2003-11-03 | 2008-09-10 | Бейцзин Санбио Байотек Ко., Лтд. | Рекомбинантный белок, обладающий противораковым действием, кодирующий его ген и его применение |
| CA2544473C (en) | 2003-11-03 | 2013-08-13 | Beijing Sunbio Biotech Co., Ltd. | A recombinant protein having an anti-cancer effect, its encoding gene and uses thereof |
| WO2005095973A2 (en) | 2004-03-25 | 2005-10-13 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with g-protein coupled receptor 54 (gpr54) |
| EP1750513A4 (en) | 2004-04-23 | 2009-07-22 | Serono Lab | USE OF GPCR54 LIGANDS FOR THE TREATMENT OF BARRENESS |
| WO2006001499A2 (en) | 2004-06-25 | 2006-01-05 | Takeda Pharmaceutical Company Limited | Metastin derivatives and use thereof |
| WO2007084211A2 (en) | 2005-11-11 | 2007-07-26 | The General Hospital Corporation | Use of gpr54 ligands for treatment of reproductive disorders, proliferative disorders, and for contraception |
| TWI386417B (zh) | 2005-12-22 | 2013-02-21 | Takeda Pharmaceutical | 轉移抑素衍生物及其用途 |
| US20090099334A1 (en) | 2005-12-22 | 2009-04-16 | Takeda Pharmaceutical Company Limited | Metastin derivatives and use thereof |
| US8404643B2 (en) | 2005-12-22 | 2013-03-26 | Takeda Pharmaceutical Company Limited | Metastin derivatives and use thereof |
| US20090093615A1 (en) | 2005-12-22 | 2009-04-09 | Takeda Pharmaceutical Company Limited | Metastin derivatives and use thereof |
| RU2008141280A (ru) | 2006-03-20 | 2010-04-27 | Мерк энд Ко., Инк. (US) | Агонисты рецептора нейромедина u и их применение |
| WO2007109857A1 (en) | 2006-03-28 | 2007-10-04 | Biopharmica Ltd | Agent for the treatment of hormone-dependent disorders and uses thereof |
| JO3048B1 (ar) | 2006-10-25 | 2016-09-05 | Takeda Pharmaceuticals Co | مشتقات متاستين واستخدامها |
| US20100286035A1 (en) | 2007-10-05 | 2010-11-11 | Takeda Pharmaceutical Company Limited | Neuromedin u derivative |
| EP2277900A4 (en) | 2008-04-24 | 2011-08-03 | Takeda Pharmaceutical | METASTINE DERIVATIVE AND ITS USE |
| EP2340047A1 (en) | 2008-09-19 | 2011-07-06 | Nektar Therapeutics | Polymer conjugates of kiss1 peptides |
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- 2005-06-23 RU RU2006145886/04A patent/RU2006145886A/ru not_active Application Discontinuation
- 2005-06-23 CA CA002571420A patent/CA2571420A1/en not_active Abandoned
- 2005-06-23 EP EP09075257.7A patent/EP2113513B1/en not_active Expired - Lifetime
- 2005-06-23 TW TW094120917A patent/TW200607816A/zh unknown
- 2005-06-23 AU AU2005257484A patent/AU2005257484A1/en not_active Abandoned
- 2005-06-23 MX MXPA06014206A patent/MXPA06014206A/es unknown
- 2005-06-23 AR ARP050102591A patent/AR049938A1/es unknown
- 2005-06-23 SG SG200904360-5A patent/SG153865A1/en unknown
- 2005-06-23 EP EP05755666A patent/EP1758932A2/en not_active Withdrawn
- 2005-06-23 PE PE2009000637A patent/PE20091567A1/es not_active Application Discontinuation
- 2005-06-23 BR BRPI0512397-6A patent/BRPI0512397A/pt not_active IP Right Cessation
- 2005-06-23 NZ NZ552029A patent/NZ552029A/en not_active IP Right Cessation
- 2005-06-23 CN CN200910225194A patent/CN101863971A/zh active Pending
- 2005-06-23 PE PE2005000728A patent/PE20060371A1/es not_active Application Discontinuation
- 2005-06-23 CN CN200910225195A patent/CN101845091A/zh active Pending
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2006
- 2006-11-27 IL IL179640A patent/IL179640A0/en unknown
- 2006-12-21 NO NO20065957A patent/NO20065957L/no not_active Application Discontinuation
- 2006-12-22 CR CR8828A patent/CR8828A/es not_active Application Discontinuation
- 2006-12-28 MA MA29567A patent/MA28903B1/fr unknown
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2008
- 2008-09-25 JP JP2008245073A patent/JP4654284B2/ja not_active Expired - Fee Related
- 2008-10-01 US US12/286,671 patent/US8778871B2/en active Active
- 2008-12-15 CL CL2008003730A patent/CL2008003730A1/es unknown
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2009
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Also Published As
| Publication number | Publication date |
|---|---|
| US20080312155A1 (en) | 2008-12-18 |
| JP2008506632A (ja) | 2008-03-06 |
| JP4654284B2 (ja) | 2011-03-16 |
| EP2113513B1 (en) | 2016-05-18 |
| WO2006001499A3 (en) | 2006-03-02 |
| CN101863971A (zh) | 2010-10-20 |
| TW200607816A (en) | 2006-03-01 |
| PE20091567A1 (es) | 2009-11-03 |
| CL2008003730A1 (es) | 2009-05-04 |
| US7625869B2 (en) | 2009-12-01 |
| MA28903B1 (fr) | 2007-10-01 |
| SG153865A1 (en) | 2009-07-29 |
| RU2006145886A (ru) | 2008-06-27 |
| JP2009227687A (ja) | 2009-10-08 |
| PE20060371A1 (es) | 2006-06-15 |
| NO20065957L (no) | 2007-01-25 |
| WO2006001499A2 (en) | 2006-01-05 |
| US20090298765A1 (en) | 2009-12-03 |
| BRPI0512397A (pt) | 2008-03-04 |
| US8778871B2 (en) | 2014-07-15 |
| EP1758932A2 (en) | 2007-03-07 |
| EP2113513A3 (en) | 2010-11-03 |
| EP2113513A2 (en) | 2009-11-04 |
| IL179640A0 (en) | 2007-05-15 |
| MXPA06014206A (es) | 2007-02-14 |
| CA2571420A1 (en) | 2006-01-05 |
| JP2009024028A (ja) | 2009-02-05 |
| CR8828A (es) | 2007-07-19 |
| NZ552029A (en) | 2009-01-31 |
| CN101845091A (zh) | 2010-09-29 |
| AR049938A1 (es) | 2006-09-13 |
| AU2005257484A1 (en) | 2006-01-05 |
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