KR101558404B1 - 옥시토신 유사체 - Google Patents
옥시토신 유사체 Download PDFInfo
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- KR101558404B1 KR101558404B1 KR1020107024207A KR20107024207A KR101558404B1 KR 101558404 B1 KR101558404 B1 KR 101558404B1 KR 1020107024207 A KR1020107024207 A KR 1020107024207A KR 20107024207 A KR20107024207 A KR 20107024207A KR 101558404 B1 KR101558404 B1 KR 101558404B1
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- KR
- South Korea
- Prior art keywords
- compound
- phenyl
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- Prior art date
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- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical class C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 208000024891 symptom Diseases 0.000 claims abstract description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- -1 methoxy, phenyl Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 208000019901 Anxiety disease Diseases 0.000 claims description 12
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
- 208000032843 Hemorrhage Diseases 0.000 claims description 8
- 230000000740 bleeding effect Effects 0.000 claims description 8
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 8
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 208000018525 Postpartum Hemorrhage Diseases 0.000 claims description 5
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000036506 anxiety Effects 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 208000004998 Abdominal Pain Diseases 0.000 claims description 4
- 208000008035 Back Pain Diseases 0.000 claims description 4
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- 206010061218 Inflammation Diseases 0.000 claims description 4
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
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- 231100000872 sexual dysfunction Toxicity 0.000 claims description 4
- 230000029663 wound healing Effects 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 206010021718 Induced labour Diseases 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 210000002826 placenta Anatomy 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 230000001010 compromised effect Effects 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 230000006735 deficit Effects 0.000 claims 1
- 125000004212 difluorophenyl group Chemical group 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 7
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- 229920005989 resin Polymers 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 230000008878 coupling Effects 0.000 description 20
- 238000010168 coupling process Methods 0.000 description 20
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 16
- 229960005222 phenazone Drugs 0.000 description 16
- 101800000989 Oxytocin Proteins 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- 102400000050 Oxytocin Human genes 0.000 description 14
- XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 description 14
- 230000001404 mediated effect Effects 0.000 description 14
- 229960001723 oxytocin Drugs 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
- 150000001413 amino acids Chemical class 0.000 description 12
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 12
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 102000004196 processed proteins & peptides Human genes 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000004471 Glycine Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000003862 amino acid derivatives Chemical class 0.000 description 5
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- 238000003786 synthesis reaction Methods 0.000 description 5
- KLBPUVPNPAJWHZ-UMSFTDKQSA-N (2r)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KLBPUVPNPAJWHZ-UMSFTDKQSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- UBLQIESZTDNNAO-UHFFFAOYSA-N n,n-diethylethanamine;phosphoric acid Chemical compound [O-]P([O-])([O-])=O.CC[NH+](CC)CC.CC[NH+](CC)CC.CC[NH+](CC)CC UBLQIESZTDNNAO-UHFFFAOYSA-N 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
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- CBPJQFCAFFNICX-IBGZPJMESA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CC(C)C)C(O)=O)C3=CC=CC=C3C2=C1 CBPJQFCAFFNICX-IBGZPJMESA-N 0.000 description 3
- QXVFEIPAZSXRGM-DJJJIMSYSA-N (2s,3s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-methylpentanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H]([C@@H](C)CC)C(O)=O)C3=CC=CC=C3C2=C1 QXVFEIPAZSXRGM-DJJJIMSYSA-N 0.000 description 3
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
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- VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 2
- AECGEIVNZGQBJT-UHFFFAOYSA-N 3-tritylsulfanylpropanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SCCC(=O)O)C1=CC=CC=C1 AECGEIVNZGQBJT-UHFFFAOYSA-N 0.000 description 2
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- UHPQFNXOFFPHJW-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanamine Chemical compound C1=CC(C)=CC=C1C(N)C1=CC=CC=C1 UHPQFNXOFFPHJW-UHFFFAOYSA-N 0.000 description 1
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| EP08251739.2 | 2008-05-19 | ||
| EP08251739 | 2008-05-19 |
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| KR20110005705A KR20110005705A (ko) | 2011-01-18 |
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| WO2011147889A1 (en) | 2010-05-25 | 2011-12-01 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical composition for the treatment of a feeding disorder with early-onset in a patient |
| JO3400B1 (ar) * | 2010-09-30 | 2019-10-20 | Ferring Bv | مركب صيدلاني من كاربيتوسين |
| DK2935312T3 (en) | 2012-12-21 | 2018-10-22 | Hoffmann La Roche | Peptides as oxytocin agonists |
| CA2949173A1 (en) * | 2014-06-03 | 2015-12-10 | Caterina Bissantz | Peptides as oxytocin agonists |
| CR20160562A (es) * | 2014-06-06 | 2017-01-06 | Hoffmann La Roche | Péptidos como agonistas de la oxitocina |
| US10588980B2 (en) | 2014-06-23 | 2020-03-17 | Novartis Ag | Fatty acids and their use in conjugation to biomolecules |
| FI3666258T3 (fi) * | 2014-09-19 | 2024-02-09 | Ferring Bv | Menetelmä prader-willin oireyhtymän hoitamiseksi |
| CN106084015B (zh) * | 2016-08-25 | 2020-01-31 | 成都圣诺生物制药有限公司 | 一种合成卡贝缩宫素的方法 |
| WO2019032946A1 (en) | 2017-08-11 | 2019-02-14 | Ferring B.V. | PROCESS FOR PRODUCING OXYTOCIN |
| WO2019030412A1 (en) * | 2017-08-11 | 2019-02-14 | Ferring B.V. | PROCESS FOR PRODUCING PHARMACEUTICAL PREPARATION |
| CN107628975B (zh) * | 2017-09-17 | 2019-10-29 | 贵州医科大学 | 赖氨酸衍生物类组蛋白去乙酰化酶抑制剂及其合成和应用 |
| CN112969450B (zh) | 2018-09-20 | 2023-05-30 | 阿卡蒂亚药品公司 | 卡贝缩宫素药物产品及用于制备其的方法 |
| CA3112185C (en) | 2018-09-20 | 2025-10-07 | Acadia Pharmaceuticals Inc. | STABLE INTRANASAL FORMULATIONS OF CARBETOCINE |
| WO2020137880A1 (ja) * | 2018-12-27 | 2020-07-02 | 国立大学法人北海道大学 | オキシトシン誘導体及びその使用 |
| JP2023500763A (ja) * | 2019-11-04 | 2023-01-11 | フェリング ベスローテン フェンノートシャップ | 泌乳の改善のためのメロトシンの鼻腔内投与 |
| US20230265124A1 (en) * | 2020-07-27 | 2023-08-24 | Az. Bd. of Reg. on Behalf of the Univ. of Arizona | Oxytocin analogues and methods for using the same |
| EP4313106B1 (en) | 2021-03-26 | 2025-01-15 | Ot4B | Treatment of dysphagia |
| WO2024044633A2 (en) * | 2022-08-23 | 2024-02-29 | Seattle Children's Hospital (D/B/A Seattle Children's Research Institute) | Oxytocin derivatives and methods of use |
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Patent Citations (2)
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| WO2003072597A1 (en) | 2002-02-27 | 2003-09-04 | Ferring Bv | Intermediates and methods for making heptapeptide oxytocin analogues |
| US20060247157A1 (en) | 2002-02-27 | 2006-11-02 | Ferring Bv | Methods for making intermediates and oxytocin analogues |
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| WO2009122285A8 (en) | 2009-12-10 |
| WO2009122285A1 (en) | 2009-10-08 |
| JP2011516460A (ja) | 2011-05-26 |
| AU2009233429B2 (en) | 2014-02-13 |
| US20110044905A1 (en) | 2011-02-24 |
| KR20110005705A (ko) | 2011-01-18 |
| AU2009233429A1 (en) | 2009-10-08 |
| EP2260053B1 (en) | 2014-05-14 |
| BRPI0910345A2 (pt) | 2015-10-06 |
| CN101983205B (zh) | 2015-08-19 |
| IL208039A (en) | 2016-03-31 |
| EP2626364A1 (en) | 2013-08-14 |
| IL208039A0 (en) | 2010-12-30 |
| JP5539310B2 (ja) | 2014-07-02 |
| PL2260053T3 (pl) | 2014-11-28 |
| SI2260053T1 (sl) | 2014-08-29 |
| HRP20140716T1 (hr) | 2014-08-29 |
| ES2488992T3 (es) | 2014-09-01 |
| RU2496788C2 (ru) | 2013-10-27 |
| DK2260053T3 (da) | 2014-06-23 |
| RU2010139634A (ru) | 2012-05-10 |
| NZ587817A (en) | 2012-05-25 |
| PT2260053E (pt) | 2014-08-29 |
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| CA2718148C (en) | 2017-11-07 |
| US8673841B2 (en) | 2014-03-18 |
| HK1146064A1 (en) | 2011-05-13 |
| CN101983205A (zh) | 2011-03-02 |
| EP2260053A1 (en) | 2010-12-15 |
| BRPI0910345B1 (pt) | 2021-08-17 |
| ZA201006733B (en) | 2011-06-29 |
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