JP2015526434A5 - - Google Patents
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- JP2015526434A5 JP2015526434A5 JP2015526845A JP2015526845A JP2015526434A5 JP 2015526434 A5 JP2015526434 A5 JP 2015526434A5 JP 2015526845 A JP2015526845 A JP 2015526845A JP 2015526845 A JP2015526845 A JP 2015526845A JP 2015526434 A5 JP2015526434 A5 JP 2015526434A5
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- Japan
- Prior art keywords
- compound according
- dendrimer
- branch
- group
- linker
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 97
- 239000000412 dendrimer Substances 0.000 claims description 50
- 229920000736 dendritic polymer Polymers 0.000 claims description 50
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 42
- 125000005647 linker group Chemical group 0.000 claims description 40
- 230000008685 targeting Effects 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 36
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 14
- 108010064942 Angiopep-2 Proteins 0.000 claims description 13
- 150000001413 amino acids Chemical group 0.000 claims description 13
- -1 azido-propyl Chemical group 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 10
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 7
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 7
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 7
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 7
- 239000004472 Lysine Substances 0.000 claims description 7
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 7
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 claims description 7
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 claims description 7
- 229940099500 cystamine Drugs 0.000 claims description 7
- 239000012634 fragment Substances 0.000 claims description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 7
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims description 7
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 7
- PEQHIRFAKIASBK-UHFFFAOYSA-N tetraphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PEQHIRFAKIASBK-UHFFFAOYSA-N 0.000 claims description 7
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 claims description 5
- 239000002872 contrast media Substances 0.000 claims description 5
- 239000000032 diagnostic agent Substances 0.000 claims description 5
- 229940039227 diagnostic agent Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- NLVXSWCKKBEXTG-UHFFFAOYSA-M ethenesulfonate Chemical compound [O-]S(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-M 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 102000039446 nucleic acids Human genes 0.000 claims description 5
- 108020004707 nucleic acids Proteins 0.000 claims description 5
- 150000007523 nucleic acids Chemical class 0.000 claims description 5
- 102000004169 proteins and genes Human genes 0.000 claims description 5
- 108090000623 proteins and genes Proteins 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003384 small molecules Chemical class 0.000 claims description 5
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 150000003573 thiols Chemical class 0.000 claims description 5
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 claims description 5
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 claims description 4
- 108010039918 Polylysine Proteins 0.000 claims description 4
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 4
- 229920000656 polylysine Polymers 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 125000005262 alkoxyamine group Chemical group 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 3
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 2
- 229920000333 poly(propyleneimine) Polymers 0.000 claims description 2
- 125000006308 propyl amino group Chemical group 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 description 24
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 24
- 229910052717 sulfur Inorganic materials 0.000 description 11
- 125000004434 sulfur atom Chemical group 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- JWDFQMWEFLOOED-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-(pyridin-2-yldisulfanyl)propanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCSSC1=CC=CC=N1 JWDFQMWEFLOOED-UHFFFAOYSA-N 0.000 description 2
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
- 0 C*CCC(NCCNC(CCN(CCC(NCCNC(CC*)=O)=O)CCNC(C)CCN(CCC*)CCC(NCCN(CCC(NCCNC(CC*)=O)=O)CCC(NCCNC(CC*)=O)=O)=O)=O)=O Chemical compound C*CCC(NCCNC(CCN(CCC(NCCNC(CC*)=O)=O)CCNC(C)CCN(CCC*)CCC(NCCN(CCC(NCCNC(CC*)=O)=O)CCC(NCCNC(CC*)=O)=O)=O)=O)=O 0.000 description 2
- 102100021923 Prolow-density lipoprotein receptor-related protein 1 Human genes 0.000 description 2
- 101710202113 Prolow-density lipoprotein receptor-related protein 1 Proteins 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 2
- FLCQLSRLQIPNLM-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-acetylsulfanylacetate Chemical compound CC(=O)SCC(=O)ON1C(=O)CCC1=O FLCQLSRLQIPNLM-UHFFFAOYSA-N 0.000 description 1
- AMLFJZRZIOZGPW-NSCUHMNNSA-N (e)-prop-1-en-1-amine Chemical compound C\C=C\N AMLFJZRZIOZGPW-NSCUHMNNSA-N 0.000 description 1
- WJWCWIMVMYWVNZ-UHFFFAOYSA-N 2-azidohexanoic acid Chemical group CCCCC(C(O)=O)N=[N+]=[N-] WJWCWIMVMYWVNZ-UHFFFAOYSA-N 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 210000003292 kidney cell Anatomy 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261682991P | 2012-08-14 | 2012-08-14 | |
| US61/682,991 | 2012-08-14 | ||
| PCT/CA2013/050621 WO2014026283A1 (en) | 2012-08-14 | 2013-08-14 | Peptide-dendrimer conjugates and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015526434A JP2015526434A (ja) | 2015-09-10 |
| JP2015526434A5 true JP2015526434A5 (enExample) | 2016-10-06 |
Family
ID=50101156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015526845A Pending JP2015526434A (ja) | 2012-08-14 | 2013-08-14 | ペプチド−デンドリマーコンジュゲート及びその使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9687561B2 (enExample) |
| EP (1) | EP2885318A4 (enExample) |
| JP (1) | JP2015526434A (enExample) |
| CN (1) | CN104781276A (enExample) |
| AU (1) | AU2013302270A1 (enExample) |
| CA (1) | CA2881602A1 (enExample) |
| WO (1) | WO2014026283A1 (enExample) |
Families Citing this family (30)
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| CN104781276A (zh) | 2012-08-14 | 2015-07-15 | 安吉奥开米公司 | 肽-树枝状聚合物结合物及其用途 |
| WO2016090495A1 (en) * | 2014-12-11 | 2016-06-16 | Angiochem Inc. | TARGETED α-L-IDURONIDASE CONJUGATES AND USES THEREOF |
| US10760181B2 (en) | 2015-02-24 | 2020-09-01 | City Of Hope | Chemically encoded spatially addressed library screening platforms |
| EP3307326B9 (en) | 2015-06-15 | 2021-02-24 | Angiochem Inc. | Methods for the treatment of leptomeningeal carcinomatosis |
| KR102764250B1 (ko) | 2015-09-14 | 2025-02-07 | 더 보드 오브 리젠츠 오브 더 유니버시티 오브 텍사스 시스템 | 지질양이온성 덴드리머 및 이의 용도 |
| CN108289872B (zh) * | 2015-10-29 | 2021-04-02 | 约翰霍普金斯大学 | 树枝状聚合物组合物和其在坏死性小肠结肠炎和其它胃肠道病症治疗中的用途 |
| CN106854231B (zh) * | 2015-12-09 | 2020-08-11 | 中国科学院大连化学物理研究所 | 一种硫巯化多肽的富集方法 |
| US11530243B2 (en) * | 2016-02-18 | 2022-12-20 | Veiove Animal Health Inc. | Non-cleavable substance P conjugates and methods of use thereof |
| PL417159A1 (pl) * | 2016-05-11 | 2017-11-20 | Instytut Biologii Doświadczalnej Im. Marcelego Nenckiego | Koniugaty białka prionowego z dendrymerami do zastosowania w leczeniu choroby Alzheimera |
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| CN106279635B (zh) * | 2016-08-10 | 2019-01-25 | 同济大学 | 类抗菌肽和囊泡及其制备方法和应用 |
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| CN110170055A (zh) * | 2019-06-04 | 2019-08-27 | 哈尔滨理工大学 | 一种新型双重脑缺血靶向纳米载体材料的制备方法 |
| WO2021046307A1 (en) * | 2019-09-04 | 2021-03-11 | North Carolina State University | Hybridized poly(amidoamine)-amino acid dendrimers |
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| MX2022012501A (es) * | 2020-04-06 | 2023-01-19 | Tiba Biotech Llc | Portadores para suministro eficiente de ácido nucléico. |
| AU2022208435A1 (en) | 2021-01-18 | 2023-08-10 | Conserv Bioscience Limited | Coronavirus immunogenic compositions, methods and uses thereof |
| JP7665261B2 (ja) * | 2022-08-05 | 2025-04-21 | 一丸ファルコス株式会社 | 新規ｌｒｐ１結合ペプチド |
| CN117363697A (zh) * | 2023-10-10 | 2024-01-09 | 上海烈冰生物医药科技有限公司 | 一种用于核酸捕获的高密度探针磁珠制备方法 |
| KR20260105738A (ko) | 2023-10-31 | 2026-07-07 | 티바 바이오테크 엘엘씨 | 신규 유전자 전달제 |
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| SI2453923T1 (sl) | 2009-07-14 | 2016-04-29 | Mayo Foundation For Medical Education And Research | S peptidi posredovana ne-kovalentna dostava aktivnih učinkovin preko krvno možganske bariere |
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| US9095541B2 (en) | 2009-11-24 | 2015-08-04 | Arch Cancer Therapeutics, Inc. | Brain tumor targeting peptides and methods |
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| EP2333074A1 (en) | 2009-12-14 | 2011-06-15 | Robert Steinfeld | Substances and methods for the treatment of lysosmal storage diseases |
| WO2011153642A1 (en) | 2010-06-10 | 2011-12-15 | Angiochem Inc. | Leptin and leptin analog conjugates and fusion proteins and uses thereof |
| EP2588490B1 (en) * | 2010-07-02 | 2017-02-22 | Angiochem Inc. | Short and d-amino acid-containing polypeptides for therapeutic conjugates and uses thereof |
| CN102406949B (zh) | 2010-09-21 | 2013-05-29 | 复旦大学 | 一种靶向示踪的多模式诊断纳米影像药物 |
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| CN102552928A (zh) | 2010-12-19 | 2012-07-11 | 复旦大学 | 一种治疗脑部肿瘤的双级靶向递药系统及其制备方法 |
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| WO2013185235A1 (en) | 2012-06-15 | 2013-12-19 | Angiochem Inc. | Targeted iduronidase compounds |
| CN104781276A (zh) | 2012-08-14 | 2015-07-15 | 安吉奥开米公司 | 肽-树枝状聚合物结合物及其用途 |
| US20160106856A1 (en) | 2012-08-14 | 2016-04-21 | Angiochem Inc. | Conjugates including an antibody moiety, a polypeptide that traverses the blood-brain barrier, and a cytotoxin |
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| US20160367691A1 (en) | 2013-06-06 | 2016-12-22 | Angiochem Inc. | Targeted enzyme compounds and uses thereof |
| WO2014194428A1 (en) | 2013-06-06 | 2014-12-11 | Angiochem Inc. | Targeted heparan sulfatase compounds |
-
2013
- 2013-08-14 CN CN201380053703.4A patent/CN104781276A/zh active Pending
- 2013-08-14 CA CA2881602A patent/CA2881602A1/en not_active Abandoned
- 2013-08-14 AU AU2013302270A patent/AU2013302270A1/en not_active Abandoned
- 2013-08-14 WO PCT/CA2013/050621 patent/WO2014026283A1/en not_active Ceased
- 2013-08-14 EP EP13829574.6A patent/EP2885318A4/en not_active Withdrawn
- 2013-08-14 US US14/422,165 patent/US9687561B2/en not_active Expired - Fee Related
- 2013-08-14 JP JP2015526845A patent/JP2015526434A/ja active Pending
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