JP2020529435A5 - - Google Patents
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- JP2020529435A5 JP2020529435A5 JP2020505847A JP2020505847A JP2020529435A5 JP 2020529435 A5 JP2020529435 A5 JP 2020529435A5 JP 2020505847 A JP2020505847 A JP 2020505847A JP 2020505847 A JP2020505847 A JP 2020505847A JP 2020529435 A5 JP2020529435 A5 JP 2020529435A5
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- JP
- Japan
- Prior art keywords
- compound
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- branched chain
- straight chain
- chemical formula
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 24
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 12
- IHUKVJKKTBLTEE-QMMMGPOBSA-N (2s)-2-acetamido-5-[[amino-(methylcarbamoylamino)methylidene]amino]-n-methylpentanamide Chemical group CNC(=O)NC(N)=NCCC[C@H](NC(C)=O)C(=O)NC IHUKVJKKTBLTEE-QMMMGPOBSA-N 0.000 claims description 9
- 108010016626 Dipeptides Chemical group 0.000 claims description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 6
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 6
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 6
- 235000003704 aspartic acid Nutrition 0.000 claims description 6
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229960002429 proline Drugs 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000004475 Arginine Substances 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 3
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 3
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims description 3
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 3
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 3
- 239000004472 Lysine Substances 0.000 claims description 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 3
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 3
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004473 Threonine Substances 0.000 claims description 3
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 3
- DZJXKISLUDYJSV-UHFFFAOYSA-N [N].C1CCNC1 Chemical group [N].C1CCNC1 DZJXKISLUDYJSV-UHFFFAOYSA-N 0.000 claims description 3
- 235000004279 alanine Nutrition 0.000 claims description 3
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims description 3
- 150000001413 amino acids Chemical group 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 235000018417 cysteine Nutrition 0.000 claims description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 3
- 235000013922 glutamic acid Nutrition 0.000 claims description 3
- 239000004220 glutamic acid Substances 0.000 claims description 3
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 3
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 3
- 229960000310 isoleucine Drugs 0.000 claims description 3
- 229930182817 methionine Natural products 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 3
- 239000004474 valine Substances 0.000 claims description 3
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims description 2
- 229930182821 L-proline Natural products 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000004108 freeze drying Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000002411 thermogravimetry Methods 0.000 claims 2
- 238000004458 analytical method Methods 0.000 claims 1
- 238000000113 differential scanning calorimetry Methods 0.000 claims 1
- 0 C*c1ccc(C[C@@](C(*)=O)NC(CNC([C@]2N(*C(*)=O)CCC2)=O)=O)cc1 Chemical compound C*c1ccc(C[C@@](C(*)=O)NC(CNC([C@]2N(*C(*)=O)CCC2)=O)=O)cc1 0.000 description 2
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022067393A JP2022106788A (ja) | 2018-02-28 | 2022-04-15 | 脂質化ペプチドの水溶性塩、その製造方法および用途 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862636552P | 2018-02-28 | 2018-02-28 | |
| US62/636,552 | 2018-02-28 | ||
| PCT/KR2019/002397 WO2019168357A1 (en) | 2018-02-28 | 2019-02-27 | Water soluble salts of lipidated peptides and methods for preparing and using the same |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022067393A Division JP2022106788A (ja) | 2018-02-28 | 2022-04-15 | 脂質化ペプチドの水溶性塩、その製造方法および用途 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020529435A JP2020529435A (ja) | 2020-10-08 |
| JP2020529435A5 true JP2020529435A5 (enExample) | 2021-09-24 |
| JP7104141B2 JP7104141B2 (ja) | 2022-07-20 |
Family
ID=67684306
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020505847A Active JP7104141B2 (ja) | 2018-02-28 | 2019-02-27 | 脂質化ペプチドの水溶性塩、その製造方法および用途 |
| JP2022067393A Pending JP2022106788A (ja) | 2018-02-28 | 2022-04-15 | 脂質化ペプチドの水溶性塩、その製造方法および用途 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022067393A Pending JP2022106788A (ja) | 2018-02-28 | 2022-04-15 | 脂質化ペプチドの水溶性塩、その製造方法および用途 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US11739120B2 (enExample) |
| EP (1) | EP3759070A4 (enExample) |
| JP (2) | JP7104141B2 (enExample) |
| KR (1) | KR102058853B1 (enExample) |
| CN (1) | CN110959002A (enExample) |
| MY (1) | MY200470A (enExample) |
| PH (1) | PH12020551233A1 (enExample) |
| SG (1) | SG11202007544RA (enExample) |
| TW (2) | TWI762770B (enExample) |
| WO (1) | WO2019168357A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102104507B1 (ko) * | 2019-08-23 | 2020-04-24 | 브릿지바이오테라퓨틱스(주) | 팔미토일-l-프롤릴-l-프롤릴-글리실-l-타이로신 나트륨을 포함하는 약제학적 제제 및 이의 제조방법 |
| CN111297905B (zh) * | 2020-03-18 | 2022-11-04 | 四川大学华西医院 | 一种基于皮肤前体细胞的提取物及其制备方法和用途 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1195762B (it) * | 1980-10-13 | 1988-10-27 | Reiner Alberto Real Sas | Derivati idrosolubili della cefalexina e procedimento per la loro produzione |
| DE3839127A1 (de) | 1988-11-19 | 1990-05-23 | Hoechst Ag | Pyrrolidon-2-carbonsaeure-derivate mit psychotroper wirkung |
| AUPM906594A0 (en) | 1994-10-26 | 1994-11-17 | Peptide Technology Limited | Synthetic polyunsaturated fatty acid analogues |
| ES2320316T3 (es) | 1996-05-01 | 2009-05-21 | Ortho-Mcneil Pharmaceutical, Inc. | Derivados carboxamida de pirrolidina, piperidina y hexahidroazepina utiles en el tratamiento de trastornos tromboticos. |
| EP1004578B1 (en) | 1998-11-05 | 2004-02-25 | Pfizer Products Inc. | 5-oxo-pyrrolidine-2-carboxylic acid hydroxamide derivatives |
| WO2003007876A2 (en) | 2001-06-25 | 2003-01-30 | University Of Massachusetts | N-fatty acid-amino acid conjugates and therapeutic uses |
| US20060252698A1 (en) | 2005-04-20 | 2006-11-09 | Malcolm Bruce A | Compounds for inhibiting cathepsin activity |
| US7842662B2 (en) | 2006-11-10 | 2010-11-30 | Cara Therapeutics, Inc. | Synthetic peptide amide dimers |
| EP2185516A2 (en) * | 2007-08-29 | 2010-05-19 | Pfizer Products Incorporated | Polymorphs of 3-(((4-tert-butyl-benzyl)-(pyridine-3-sulfonyl)-amino)-methyl)-phenoxy)-acetic acid sodium salt or a hydrate thereof and methods for making the same |
| WO2010059922A1 (en) * | 2008-11-21 | 2010-05-27 | Ligand Pharmaceuticals Incorporated | Pyrrolidine carboxamide compounds |
| KR101151878B1 (ko) | 2010-06-08 | 2012-05-31 | 미원상사주식회사 | 지방산 트리펩타이드염 및 이를 함유하는 항균 조성물 |
| KR101348284B1 (ko) | 2010-09-09 | 2014-01-03 | 주식회사 나이벡 | 인간 유래 세포 투과성 펩타이드와 생리활성 펩타이드 결합체 및 그 용도 |
| KR20120048864A (ko) | 2010-11-08 | 2012-05-16 | 주식회사 네오디엠 | 트리 펩타이드 유도체를 함유한 아토피 피부염 예방 및 치료용 조성물과 그 제조방법 |
| KR20130038426A (ko) | 2011-10-07 | 2013-04-18 | 성균관대학교산학협력단 | 지방산이 결합된 항당뇨 펩티드가 소수성 결합된 글리콜 키토산 히드로겔 및 이를 포함하는 당뇨병 예방 또는 치료용 약학적 조성물 |
| KR101359886B1 (ko) | 2011-12-28 | 2014-02-12 | 성균관대학교산학협력단 | 스매드 6번(Ｓｍａｄ６)으로부터 유래된 펩타이드를 유효성분으로 포함하는 패혈증 또는 패혈성 쇼크의 치료용 조성물 |
| WO2013190497A2 (en) * | 2012-06-21 | 2013-12-27 | Radikal Therapeutics Inc. | Compositions and methods for treatment of inflammatory diseases of the lung |
| CN103724204B (zh) * | 2013-11-27 | 2016-05-11 | 北京化工大学 | 一种水溶性引发剂及制备 |
| UA121890C2 (uk) * | 2015-07-08 | 2020-08-10 | Рісерч Енд Бізнес Фаундейшн Сонгюнгван Юніверсіті | Похідні карбоксамідопіролідину та способи їхнього отримання та застосування |
-
2019
- 2019-02-27 JP JP2020505847A patent/JP7104141B2/ja active Active
- 2019-02-27 EP EP19759922.8A patent/EP3759070A4/en active Pending
- 2019-02-27 MY MYPI2020004110A patent/MY200470A/en unknown
- 2019-02-27 SG SG11202007544RA patent/SG11202007544RA/en unknown
- 2019-02-27 TW TW108106759A patent/TWI762770B/zh active
- 2019-02-27 CN CN201980003752.4A patent/CN110959002A/zh active Pending
- 2019-02-27 TW TW110130498A patent/TWI811767B/zh active
- 2019-02-27 WO PCT/KR2019/002397 patent/WO2019168357A1/en not_active Ceased
- 2019-02-27 KR KR1020190023508A patent/KR102058853B1/ko active Active
- 2019-02-28 US US16/288,571 patent/US11739120B2/en active Active
-
2020
- 2020-08-10 PH PH12020551233A patent/PH12020551233A1/en unknown
-
2022
- 2022-04-15 JP JP2022067393A patent/JP2022106788A/ja active Pending
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