JP2012524775A5 - - Google Patents
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- Publication number
- JP2012524775A5 JP2012524775A5 JP2012506651A JP2012506651A JP2012524775A5 JP 2012524775 A5 JP2012524775 A5 JP 2012524775A5 JP 2012506651 A JP2012506651 A JP 2012506651A JP 2012506651 A JP2012506651 A JP 2012506651A JP 2012524775 A5 JP2012524775 A5 JP 2012524775A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alpha
- naturally occurring
- phe
- formula
- 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.)
- Granted
Links
- 235000001014 amino acid Nutrition 0.000 claims 22
- 150000001413 amino acids Chemical class 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 22
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims 18
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 claims 15
- 229960002685 biotin Drugs 0.000 claims 12
- 239000011616 biotin Substances 0.000 claims 12
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 11
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 10
- 208000001132 Osteoporosis Diseases 0.000 claims 9
- 235000020958 biotin Nutrition 0.000 claims 9
- MXECDVKIKUSSNC-JTQLQIEISA-N (2s)-2-amino-3-(2-fluorophenyl)-2-methylpropanoic acid Chemical compound OC(=O)[C@](N)(C)CC1=CC=CC=C1F MXECDVKIKUSSNC-JTQLQIEISA-N 0.000 claims 8
- FMUMEWVNYMUECA-LURJTMIESA-N (2s)-2-azaniumyl-5-methylhexanoate Chemical compound CC(C)CC[C@H](N)C(O)=O FMUMEWVNYMUECA-LURJTMIESA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- WEWMIQSBLMNNMQ-JTQLQIEISA-N (2s)-2-amino-3-(2,6-difluorophenyl)-2-methylpropanoic acid Chemical compound OC(=O)[C@](N)(C)CC1=C(F)C=CC=C1F WEWMIQSBLMNNMQ-JTQLQIEISA-N 0.000 claims 6
- XOQZTHUXZWQXOK-UHFFFAOYSA-N 2-azaniumyl-5-phenylpentanoate Chemical compound OC(=O)C(N)CCCC1=CC=CC=C1 XOQZTHUXZWQXOK-UHFFFAOYSA-N 0.000 claims 6
- XIGSAGMEBXLVJJ-YFKPBYRVSA-N L-homocitrulline Chemical compound NC(=O)NCCCC[C@H]([NH3+])C([O-])=O XIGSAGMEBXLVJJ-YFKPBYRVSA-N 0.000 claims 6
- GPYTYOMSQHBYTK-LURJTMIESA-N (2s)-2-azaniumyl-2,3-dimethylbutanoate Chemical compound CC(C)[C@](C)([NH3+])C([O-])=O GPYTYOMSQHBYTK-LURJTMIESA-N 0.000 claims 5
- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical compound OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 239000004475 Arginine Substances 0.000 claims 4
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 4
- 239000004472 Lysine Substances 0.000 claims 4
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 4
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 4
- -1 etionine (EtMet) Chemical compound 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 229960003104 ornithine Drugs 0.000 claims 4
- WOXWUZCRWJWTRT-UHFFFAOYSA-N 1-amino-1-cyclohexanecarboxylic acid Chemical compound OC(=O)C1(N)CCCCC1 WOXWUZCRWJWTRT-UHFFFAOYSA-N 0.000 claims 3
- NILQLFBWTXNUOE-UHFFFAOYSA-N 1-aminocyclopentanecarboxylic acid Chemical compound OC(=O)C1(N)CCCC1 NILQLFBWTXNUOE-UHFFFAOYSA-N 0.000 claims 3
- MVAJOGCZNRWTRF-UHFFFAOYSA-N 2-amino-2-methyl-5-phenylpentanoic acid Chemical compound OC(=O)C(N)(C)CCCC1=CC=CC=C1 MVAJOGCZNRWTRF-UHFFFAOYSA-N 0.000 claims 3
- SNDPXSYFESPGGJ-UHFFFAOYSA-N 2-aminopentanoic acid Chemical compound CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 claims 3
- NYCRCTMDYITATC-UHFFFAOYSA-N 2-fluorophenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1F NYCRCTMDYITATC-UHFFFAOYSA-N 0.000 claims 3
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims 3
- QUOGESRFPZDMMT-UHFFFAOYSA-N L-Homoarginine Natural products OC(=O)C(N)CCCCNC(N)=N QUOGESRFPZDMMT-UHFFFAOYSA-N 0.000 claims 3
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims 3
- QUOGESRFPZDMMT-YFKPBYRVSA-N L-homoarginine Chemical compound OC(=O)[C@@H](N)CCCCNC(N)=N QUOGESRFPZDMMT-YFKPBYRVSA-N 0.000 claims 3
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 claims 3
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims 3
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- HYOWVAAEQCNGLE-JTQLQIEISA-N alpha-methyl-L-phenylalanine Chemical compound OC(=O)[C@](N)(C)CC1=CC=CC=C1 HYOWVAAEQCNGLE-JTQLQIEISA-N 0.000 claims 3
- 229960002173 citrulline Drugs 0.000 claims 3
- 235000013477 citrulline Nutrition 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- LEVLUBIPMJQYHH-QMMMGPOBSA-N (2s)-2-(difluoroamino)-3-phenylpropanoic acid Chemical compound OC(=O)[C@@H](N(F)F)CC1=CC=CC=C1 LEVLUBIPMJQYHH-QMMMGPOBSA-N 0.000 claims 2
- LWHHAVWYGIBIEU-LURJTMIESA-N (2s)-2-methylpyrrolidin-1-ium-2-carboxylate Chemical compound [O-]C(=O)[C@]1(C)CCC[NH2+]1 LWHHAVWYGIBIEU-LURJTMIESA-N 0.000 claims 2
- 206010010356 Congenital anomaly Diseases 0.000 claims 2
- AKCRVYNORCOYQT-YFKPBYRVSA-N N-methyl-L-valine Chemical compound CN[C@@H](C(C)C)C(O)=O AKCRVYNORCOYQT-YFKPBYRVSA-N 0.000 claims 2
- 206010031252 Osteomyelitis Diseases 0.000 claims 2
- RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 claims 2
- RJFAYQIBOAGBLC-UHFFFAOYSA-N Selenomethionine Natural products C[Se]CCC(N)C(O)=O RJFAYQIBOAGBLC-UHFFFAOYSA-N 0.000 claims 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- VZSTVUJXUYNIOQ-UHFFFAOYSA-N alpha-amino-gamma-cyanobutanoic acid Chemical compound OC(=O)C(N)CCC#N VZSTVUJXUYNIOQ-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000002124 endocrine Effects 0.000 claims 2
- 230000002068 genetic effect Effects 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229960002718 selenomethionine Drugs 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- LKZQHZQXROBVOO-ZETCQYMHSA-N (2s)-2-amino-2-methylhexanoic acid Chemical compound CCCC[C@](C)(N)C(O)=O LKZQHZQXROBVOO-ZETCQYMHSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- CDUUKBXTEOFITR-BYPYZUCNSA-N 2-methyl-L-serine Chemical compound OC[C@@]([NH3+])(C)C([O-])=O CDUUKBXTEOFITR-BYPYZUCNSA-N 0.000 claims 1
- 206010065687 Bone loss Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims 1
- 102100032256 Parathyroid hormone/parathyroid hormone-related peptide receptor Human genes 0.000 claims 1
- 101710180613 Parathyroid hormone/parathyroid hormone-related peptide receptor Proteins 0.000 claims 1
- 208000025747 Rheumatic disease Diseases 0.000 claims 1
- 201000002661 Spondylitis Diseases 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- CDUUKBXTEOFITR-UHFFFAOYSA-N alpha-methylserine Natural products OCC([NH3+])(C)C([O-])=O CDUUKBXTEOFITR-UHFFFAOYSA-N 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002458 infectious effect Effects 0.000 claims 1
- 230000003902 lesion Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 208000001685 postmenopausal osteoporosis Diseases 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1095/MUM/2009 | 2009-04-24 | ||
| IN1095MU2009 | 2009-04-24 | ||
| IN225MU2010 | 2010-01-28 | ||
| IN225/MUM/2010 | 2010-01-28 | ||
| PCT/IN2010/000264 WO2010128521A2 (en) | 2009-04-24 | 2010-04-26 | Short-chain peptides as parathyroid hormone (pth) receptor agonist |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012524775A JP2012524775A (ja) | 2012-10-18 |
| JP2012524775A5 true JP2012524775A5 (https=) | 2013-05-02 |
| JP5744844B2 JP5744844B2 (ja) | 2015-07-08 |
Family
ID=43050579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012506651A Expired - Fee Related JP5744844B2 (ja) | 2009-04-24 | 2010-04-26 | 副甲状腺ホルモン（ｐｔｈ）受容体アゴニストとしての短鎖ペプチド |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8383581B2 (https=) |
| EP (1) | EP2421893A2 (https=) |
| JP (1) | JP5744844B2 (https=) |
| KR (1) | KR101451470B1 (https=) |
| CN (1) | CN102405229A (https=) |
| AU (1) | AU2010245642A1 (https=) |
| BR (1) | BRPI1008103A2 (https=) |
| CA (1) | CA2757874C (https=) |
| EA (1) | EA022212B1 (https=) |
| IL (1) | IL215625A (https=) |
| MX (1) | MX2011010968A (https=) |
| NZ (1) | NZ595437A (https=) |
| SG (1) | SG174532A1 (https=) |
| WO (1) | WO2010128521A2 (https=) |
| ZA (1) | ZA201107078B (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928487A (en) * | 1974-11-27 | 1975-12-23 | Standard Oil Co | Alkylation process utilizing hydrofluoric acid with a minor amount of fluorosulfuric acid |
| UY32099A (es) | 2008-09-11 | 2010-04-30 | Enanta Pharm Inc | Inhibidores macrocíclicos de serina proteasas de hepatitis c |
| CA2822556A1 (en) | 2010-12-30 | 2012-07-05 | Enanta Pharmaceuticals, Inc | Macrocyclic hepatitis c serine protease inhibitors |
| EA201390988A1 (ru) | 2010-12-30 | 2014-04-30 | Энанта Фармасьютикалз, Инк. | Фенантридиновые макроциклические ингибиторы сериновой протеазы вируса гепатита c |
| WO2012120532A2 (en) | 2011-02-02 | 2012-09-13 | Cadila Healthcare Limited | Cyclic short chain peptides |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
| WO2024187241A1 (en) * | 2023-03-16 | 2024-09-19 | The Florey Institute Of Neuroscience And Mental Health | Stapled peptides |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4486256B2 (ja) * | 1998-10-22 | 2010-06-23 | ザ・ジェネラル・ホスピタル・コーポレイション | 副甲状腺ホルモン（ＰＴＨ）および副甲状腺ホルモン関連ペプチド（ＰＴＨｒＰ）の生物活性ペプチドおよびペプチド誘導体 |
| ATE412670T1 (de) * | 1999-09-29 | 2008-11-15 | Gen Hospital Corp | Parathyroid hormon (pth) polypeptidderivate |
| WO2001023521A2 (en) * | 1999-09-29 | 2001-04-05 | The General Hospital Corporation | Polypeptide derivatives of parathyroid hormone (pth) |
| AU2002339843B2 (en) * | 2001-07-23 | 2007-12-06 | The General Hospital Corporation | Conformationally constrained parathyroid hormone (PTH) analogs |
| AU2002951372A0 (en) | 2002-09-13 | 2002-09-26 | St Vincent's Institute Of Medical Research | Parathyroid hormone-like polypeptides |
| WO2004067021A1 (en) * | 2003-01-24 | 2004-08-12 | Gardella Thomas J | Conformationally constrained parathyroid hormone (pth) analogs with lactam bridges |
| US7795220B2 (en) | 2003-03-19 | 2010-09-14 | The General Hospital Corporation | Conformationally constrained parathyroid hormones with alpha-helix stabilizers |
| JP4871128B2 (ja) | 2003-07-17 | 2012-02-08 | ザ ジェネラル ホスピタル コーポレイション | 高次構造的に制約された副甲状腺ホルモン（ｐｔｈ）アナログ |
| WO2005077959A1 (en) | 2004-02-11 | 2005-08-25 | Smithkline Beecham Corporation | Pth agonists |
| US20070123548A1 (en) | 2004-02-11 | 2007-05-31 | Cowan David J | Pth agonists |
| ITMI20041440A1 (it) | 2004-07-19 | 2004-10-19 | Abiogen Pharma Spa | Peptidi analoghi del pth-1-11 |
| AU2006343306A1 (en) | 2005-09-06 | 2007-11-15 | Zelos Therapeutics, Inc. | Parathyroid hormone analogues and methods of use |
| EP1961765A1 (en) | 2006-12-08 | 2008-08-27 | Zealand Pharma A/S | Truncated PTH peptides with a cyclic conformation |
| CN104072606B (zh) * | 2007-08-01 | 2017-09-22 | 总医院有限公司 | 利用g蛋白偶联受体和相关组合物的筛选方法 |
-
2010
- 2010-04-26 NZ NZ595437A patent/NZ595437A/en not_active IP Right Cessation
- 2010-04-26 KR KR1020117026057A patent/KR101451470B1/ko not_active Expired - Fee Related
- 2010-04-26 JP JP2012506651A patent/JP5744844B2/ja not_active Expired - Fee Related
- 2010-04-26 EP EP10747683.0A patent/EP2421893A2/en not_active Withdrawn
- 2010-04-26 US US13/259,706 patent/US8383581B2/en not_active Expired - Fee Related
- 2010-04-26 BR BRPI1008103A patent/BRPI1008103A2/pt not_active IP Right Cessation
- 2010-04-26 SG SG2011068863A patent/SG174532A1/en unknown
- 2010-04-26 AU AU2010245642A patent/AU2010245642A1/en not_active Abandoned
- 2010-04-26 EA EA201171292A patent/EA022212B1/ru not_active IP Right Cessation
- 2010-04-26 MX MX2011010968A patent/MX2011010968A/es active IP Right Grant
- 2010-04-26 CA CA2757874A patent/CA2757874C/en not_active Expired - Fee Related
- 2010-04-26 CN CN2010800175792A patent/CN102405229A/zh active Pending
- 2010-04-26 WO PCT/IN2010/000264 patent/WO2010128521A2/en not_active Ceased
-
2011
- 2011-09-28 ZA ZA2011/07078A patent/ZA201107078B/en unknown
- 2011-10-09 IL IL215625A patent/IL215625A/en not_active IP Right Cessation
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