CA2573612A1 - Polyaminoacides fonctionnalises par des greffons hydrophobes portant une charge anionique et leurs applications notamment therapeutiques - Google Patents
Polyaminoacides fonctionnalises par des greffons hydrophobes portant une charge anionique et leurs applications notamment therapeutiques Download PDFInfo
- Publication number
- CA2573612A1 CA2573612A1 CA002573612A CA2573612A CA2573612A1 CA 2573612 A1 CA2573612 A1 CA 2573612A1 CA 002573612 A CA002573612 A CA 002573612A CA 2573612 A CA2573612 A CA 2573612A CA 2573612 A1 CA2573612 A1 CA 2573612A1
- Authority
- CA
- Canada
- Prior art keywords
- cndot
- hydrophobic
- group
- polyamino acid
- polyamino
- 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.)
- Abandoned
Links
- 229920001308 poly(aminoacid) Polymers 0.000 title claims abstract description 46
- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 40
- 125000000129 anionic group Chemical group 0.000 title claims abstract description 20
- 230000001225 therapeutic effect Effects 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims abstract description 38
- 239000000725 suspension Substances 0.000 claims abstract description 14
- 125000001165 hydrophobic group Chemical group 0.000 claims abstract description 12
- 239000002537 cosmetic Substances 0.000 claims abstract description 9
- 235000005911 diet Nutrition 0.000 claims abstract description 5
- 230000000378 dietary effect Effects 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 69
- 239000000243 solution Substances 0.000 claims description 32
- 230000006870 function Effects 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 23
- 235000018102 proteins Nutrition 0.000 claims description 21
- 102000004169 proteins and genes Human genes 0.000 claims description 21
- 108090000623 proteins and genes Proteins 0.000 claims description 21
- 150000001413 amino acids Chemical group 0.000 claims description 20
- -1 amine cations Chemical class 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 229940024606 amino acid Drugs 0.000 claims description 12
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
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- 150000007942 carboxylates Chemical group 0.000 claims description 7
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 7
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- 125000002091 cationic group Chemical group 0.000 claims description 5
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- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
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- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
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- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 3
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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- 150000001261 hydroxy acids Chemical class 0.000 claims description 3
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- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 2
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
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- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| FR0408478 | 2004-07-30 | ||
| FR0408478A FR2873704B1 (fr) | 2004-07-30 | 2004-07-30 | Polyaminoacides fonctionnalises par des greffons hydrophobes portant une charge anionique et leurs applications notamment therapeutiques |
| PCT/FR2005/050610 WO2006021710A1 (fr) | 2004-07-30 | 2005-07-25 | Polyaminoacides fonctionnalises par des greffons hydrophobes portant une charge anionique et leurs applications notamment therapeutiques |
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| CA2573612A1 true CA2573612A1 (fr) | 2006-03-02 |
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| CA002573612A Abandoned CA2573612A1 (fr) | 2004-07-30 | 2005-07-25 | Polyaminoacides fonctionnalises par des greffons hydrophobes portant une charge anionique et leurs applications notamment therapeutiques |
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| CA (1) | CA2573612A1 (enExample) |
| DE (1) | DE602005017903D1 (enExample) |
| FR (1) | FR2873704B1 (enExample) |
| WO (1) | WO2006021710A1 (enExample) |
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| FR2915684B1 (fr) * | 2007-05-03 | 2011-01-14 | Flamel Tech Sa | Particules a base de polyelectrolytes et de principe actif a liberation modifiee et formulations pharmaceutiques contenant ces particules |
| US7999040B2 (en) | 2007-09-25 | 2011-08-16 | Nanochem Solutions, Inc. | Method of making graft copolymers from sodium poly(aspartate) and the resulting graft copolymer |
| WO2009041913A1 (en) * | 2007-09-26 | 2009-04-02 | Thorsson Limited | Colloidal fertilizer and related methods |
| WO2009133968A1 (ja) * | 2008-04-30 | 2009-11-05 | 国立大学法人東京大学 | 電荷変換型三元系ポリプレックス |
| WO2011097727A1 (en) | 2010-02-10 | 2011-08-18 | Queen's University At Kingston | Water with switchable ionic strength |
| JP2013234207A (ja) * | 2010-08-31 | 2013-11-21 | Jsr Corp | 新規重合体及び新規ｎ−カルボキシアミノ酸無水物、ならびにそれらの製造方法 |
| CN103459439B (zh) | 2010-12-15 | 2017-09-12 | 金斯顿女王大学 | 使用具有可转换的离子强度的水的系统和方法 |
| CN111698999A (zh) * | 2017-12-06 | 2020-09-22 | 阿道恰公司 | 包含至少一种pi在5.8与8.5之间的基础胰岛素和带有羧酸根电荷及疏水基的共聚氨基酸的ph为7的可注射溶液 |
| KR20200106890A (ko) * | 2017-12-07 | 2020-09-15 | 아도시아 | 아밀린, 아밀린 작용제 수용체 또는 아밀린 유사체 및 코-폴리아미노산을 포함하는 주사용 수용액 형태의 조성물 |
| EP3740195A1 (fr) * | 2017-12-07 | 2020-11-25 | Adocia | Compositions sous forme d'une solution aqueuse injectable comprenant de l'amyline, un agoniste au recepteur de l'amyline ou un analogue d'amyline et un co-polyaminoacide |
| BR112020011570A2 (pt) | 2017-12-07 | 2020-12-08 | Adocia | Solução injetável a um ph 7 compreendendo pelo menos uma insulina basal apresentando um pi entre 5,8 e 8,5 e um co-poliaminoácido contendo cargas de carboxilato e radicais hidrofóbicos |
| IL275146B2 (en) | 2017-12-07 | 2025-01-01 | Adocia | Preparations in the form of an aqueous solution for injection comprising amylin, an amylin receptor agonist or an amylin analog and a copolyamino acid |
| KR20240171197A (ko) | 2017-12-07 | 2024-12-06 | 아도시아 | pI가 5.8 내지 8.5인 적어도 1종의 기저 인슐린, 및 카복실산염 전하 및 소수성 라디칼을 보유하는 코-폴리아미노산을 포함하는 pH 7의 주사용 용액 |
| CN109498548B (zh) * | 2018-12-11 | 2021-09-24 | 吉林化工学院 | 一种蛋白质与光敏剂共传递pH响应性聚氨基酸纳米凝胶及其制备方法 |
| WO2022194759A1 (en) * | 2021-03-18 | 2022-09-22 | Agfa-Gevaert Nv | Poly(amino acid) based capsules |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4351337A (en) * | 1973-05-17 | 1982-09-28 | Arthur D. Little, Inc. | Biodegradable, implantable drug delivery device, and process for preparing and using the same |
| JPS60100516A (ja) * | 1983-11-04 | 1985-06-04 | Takeda Chem Ind Ltd | 徐放型マイクロカプセルの製造法 |
| DE3581471D1 (de) * | 1984-10-19 | 1991-02-28 | Battelle Memorial Institute | Durch mikroorganismen abbaubares polypeptid und seine verwendung fuer die fortschreitende abgabe von medikamenten. |
| CH667874A5 (fr) * | 1985-12-19 | 1988-11-15 | Battelle Memorial Institute | Polypeptide synthetique biodegradable et son utilisation pour la preparation de medicaments. |
| KR940003548U (ko) * | 1992-08-14 | 1994-02-21 | 김형술 | 세탁물 건조기 |
| US6153193A (en) * | 1993-04-28 | 2000-11-28 | Supratek Pharma Inc. | Compositions for targeting biological agents |
| FR2732218B1 (fr) * | 1995-03-28 | 1997-08-01 | Flamel Tech Sa | Particules a base de polyaminoacide(s) et susceptibles d'etre utilisees comme vecteurs de principe(s) actif(s) et leurs procedes de preparation |
| FR2786098B1 (fr) * | 1998-11-20 | 2003-05-30 | Flamel Tech Sa | Particules a base de polyaminoacide(s) et susceptibles d'etre utilisees comme vecteurs de principe(s) actif(s), suspension colloidale les comprenant et leurs procedes de fabrication |
| BR0211650A (pt) * | 2001-08-03 | 2004-07-13 | Procter & Gamble | Derivados de poliaspartato para uso em composições detergentes |
| JP2003327693A (ja) * | 2002-05-15 | 2003-11-19 | Mitsuru Akashi | 親−疎水性修飾ポリ（γ−グルタミン酸） |
| FR2840614B1 (fr) * | 2002-06-07 | 2004-08-27 | Flamel Tech Sa | Polyaminoacides fonctionnalises par de l'alpha-tocopherol et leurs applications notamment therapeutiques |
| FR2843117B1 (fr) * | 2002-07-30 | 2004-10-15 | Flamel Tech Sa | Polyaminoacides fonctionnalises par au moins un groupement hydrophobe et leurs applications notamment therapeutiques |
| AU2003294056A1 (en) * | 2002-12-04 | 2004-07-29 | Flamel Technologies | Polyamino acids functionalized by at least one (oligo)amino acid group and therapeutic uses |
| FR2855521B1 (fr) * | 2003-05-28 | 2005-08-05 | Flamel Tech Sa | Polyaminoacides fonctionnalises par au moins un groupement h ydrophobe et leurs applications notamment therapeutiques. |
| FR2873703B1 (fr) * | 2004-07-30 | 2006-12-08 | Flamel Technologies Sa | Polyaminoacides branches, fonctionnalises par des groupements hydrophobes et leurs applications notamment therapeutiques |
-
2004
- 2004-07-30 FR FR0408478A patent/FR2873704B1/fr not_active Expired - Fee Related
-
2005
- 2005-07-25 DE DE602005017903T patent/DE602005017903D1/de not_active Expired - Lifetime
- 2005-07-25 US US11/658,803 patent/US20100098656A1/en not_active Abandoned
- 2005-07-25 CA CA002573612A patent/CA2573612A1/fr not_active Abandoned
- 2005-07-25 WO PCT/FR2005/050610 patent/WO2006021710A1/fr not_active Ceased
- 2005-07-25 AT AT05792029T patent/ATE449806T1/de not_active IP Right Cessation
- 2005-07-25 EP EP05792029A patent/EP1773914B9/fr not_active Expired - Lifetime
- 2005-07-25 JP JP2007523129A patent/JP5324093B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FR2873704B1 (fr) | 2006-12-08 |
| DE602005017903D1 (de) | 2010-01-07 |
| JP2008508389A (ja) | 2008-03-21 |
| FR2873704A1 (fr) | 2006-02-03 |
| EP1773914B9 (fr) | 2010-03-31 |
| US20100098656A1 (en) | 2010-04-22 |
| WO2006021710A1 (fr) | 2006-03-02 |
| JP5324093B2 (ja) | 2013-10-23 |
| EP1773914A1 (fr) | 2007-04-18 |
| ATE449806T1 (de) | 2009-12-15 |
| EP1773914B1 (fr) | 2009-11-25 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |