JPWO2019157138A5 - - Google Patents
Download PDFInfo
- Publication number
- JPWO2019157138A5 JPWO2019157138A5 JP2020542562A JP2020542562A JPWO2019157138A5 JP WO2019157138 A5 JPWO2019157138 A5 JP WO2019157138A5 JP 2020542562 A JP2020542562 A JP 2020542562A JP 2020542562 A JP2020542562 A JP 2020542562A JP WO2019157138 A5 JPWO2019157138 A5 JP WO2019157138A5
- Authority
- JP
- Japan
- Prior art keywords
- liposome
- group
- pemetrexed
- glutamil
- oxidized
- 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.)
- Pending
Links
- 239000002502 liposome Substances 0.000 claims 30
- WBXPDJSOTKVWSJ-ZDUSSCGKSA-N pemetrexed Chemical compound C=1NC=2NC(N)=NC(=O)C=2C=1CCC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 WBXPDJSOTKVWSJ-ZDUSSCGKSA-N 0.000 claims 23
- 229960005079 pemetrexed Drugs 0.000 claims 23
- 239000000203 mixture Substances 0.000 claims 19
- 229920001223 polyethylene glycol Polymers 0.000 claims 11
- 108090001123 antibodies Proteins 0.000 claims 9
- 102000004965 antibodies Human genes 0.000 claims 9
- 108010040003 polyglutamine Proteins 0.000 claims 8
- 229920000155 polyglutamine Polymers 0.000 claims 8
- 239000002202 Polyethylene glycol Substances 0.000 claims 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol 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 4
- 102000010449 Folate receptor beta Human genes 0.000 claims 4
- 108050001930 Folate receptor beta Proteins 0.000 claims 4
- 102000006815 Folate receptors Human genes 0.000 claims 4
- 108020005243 Folate receptors Proteins 0.000 claims 4
- 239000000839 emulsion Substances 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- -1 2-hydroxypropyl Chemical group 0.000 claims 3
- 229920002498 Beta-glucan Polymers 0.000 claims 3
- 239000000427 antigen Substances 0.000 claims 3
- 102000038129 antigens Human genes 0.000 claims 3
- 108091007172 antigens Proteins 0.000 claims 3
- 238000001125 extrusion Methods 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- LVNGJLRDBYCPGB-UHFFFAOYSA-N 1,2-distearoylphosphatidylethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCCCCCCCCCCCC LVNGJLRDBYCPGB-UHFFFAOYSA-N 0.000 claims 2
- 238000010146 3D printing Methods 0.000 claims 2
- 229940107161 Cholesterol Drugs 0.000 claims 2
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-Mannitol Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 claims 2
- 102000010451 Folate receptor alpha Human genes 0.000 claims 2
- 108050001931 Folate receptor alpha Proteins 0.000 claims 2
- 102100012474 IZUMO1R Human genes 0.000 claims 2
- 101710002465 IZUMO1R Proteins 0.000 claims 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 2
- 102100011593 PSMA7 Human genes 0.000 claims 2
- 101710033516 PSMA7 Proteins 0.000 claims 2
- HDTRYLNUVZCQOY-LIZSDCNHSA-N Trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims 2
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims 2
- 125000000129 anionic group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 235000012000 cholesterol Nutrition 0.000 claims 2
- 230000001809 detectable Effects 0.000 claims 2
- 239000008121 dextrose Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 238000005516 engineering process Methods 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 claims 2
- 230000036571 hydration Effects 0.000 claims 2
- 238000006703 hydration reaction Methods 0.000 claims 2
- 230000003344 immunostimulant Effects 0.000 claims 2
- 239000003022 immunostimulating agent Substances 0.000 claims 2
- 238000002347 injection Methods 0.000 claims 2
- 239000007924 injection Substances 0.000 claims 2
- 239000000594 mannitol Substances 0.000 claims 2
- 235000010355 mannitol Nutrition 0.000 claims 2
- 239000003550 marker Substances 0.000 claims 2
- 239000012528 membrane Substances 0.000 claims 2
- 230000001264 neutralization Effects 0.000 claims 2
- 229920002401 polyacrylamide Polymers 0.000 claims 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 239000010409 thin film Substances 0.000 claims 2
- 102000002689 toll-like receptors Human genes 0.000 claims 2
- 108020000411 toll-like receptors Proteins 0.000 claims 2
- FYGDTMLNYKFZSV-WFYNLLPOSA-N (2S,3R,4S,5S,6R)-2-[(2R,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-WFYNLLPOSA-N 0.000 claims 1
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 claims 1
- CDZVJFRXJAUXPP-AREMUKBSSA-N 2-O-glutaroyl-1-O-palmitoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCC(O)=O)COP([O-])(=O)OCC[N+](C)(C)C CDZVJFRXJAUXPP-AREMUKBSSA-N 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L Calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims 1
- OLESAACUTLOWQZ-UHFFFAOYSA-L Carboplatin Chemical compound O=C1O[Pt]([N]([H])([H])[H])([N]([H])([H])[H])OC(=O)C11CCC1 OLESAACUTLOWQZ-UHFFFAOYSA-L 0.000 claims 1
- 229960004562 Carboplatin Drugs 0.000 claims 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 1
- 230000036947 Dissociation constant Effects 0.000 claims 1
- 229960000304 Folic Acid Drugs 0.000 claims 1
- OVBPIULPVIDEAO-LBPRGKRZSA-N Folic acid Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims 1
- 206010017758 Gastric cancer Diseases 0.000 claims 1
- 239000007995 HEPES buffer Substances 0.000 claims 1
- 210000000987 Immune System Anatomy 0.000 claims 1
- 150000008575 L-amino acids Chemical class 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N Methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinylpyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- 108010020346 Polyglutamic Acid Proteins 0.000 claims 1
- 229920001451 Polypropylene glycol Polymers 0.000 claims 1
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 1
- CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- 239000001639 calcium acetate Substances 0.000 claims 1
- 229960005147 calcium acetate Drugs 0.000 claims 1
- 235000011092 calcium acetate Nutrition 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 230000001082 cryoprotectant Effects 0.000 claims 1
- 239000002577 cryoprotective agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 201000009910 diseases by infectious agent Diseases 0.000 claims 1
- BPSMYQFMCXXNPC-MFCPCZTFSA-N eritoran Chemical class O[C@H]1[C@H](OCCCCCCCCCC)[C@@H](NC(=O)CC(=O)CCCCCCCCCCC)[C@@H](OP(O)(O)=O)O[C@@H]1CO[C@H]1[C@H](NC(=O)CCCCCCCCC\C=C/CCCCCC)[C@@H](OCC[C@@H](CCCCCCC)OC)[C@H](OP(O)(O)=O)[C@@H](COC)O1 BPSMYQFMCXXNPC-MFCPCZTFSA-N 0.000 claims 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims 1
- 235000019152 folic acid Nutrition 0.000 claims 1
- 239000011724 folic acid Substances 0.000 claims 1
- 125000003929 folic acid group Chemical group 0.000 claims 1
- 229920000370 gamma-poly(glutamate) polymer Polymers 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims 1
- 108010071584 oxidized low density lipoprotein Proteins 0.000 claims 1
- 229960002621 pembrolizumab Drugs 0.000 claims 1
- 108010026276 pembrolizumab Proteins 0.000 claims 1
- 125000001095 phosphatidyl group Chemical group 0.000 claims 1
- 229920000068 poly(2-ethyl-2-oxazoline) Polymers 0.000 claims 1
- 229920000773 poly(2-methyl-2-oxazoline) polymer Polymers 0.000 claims 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims 1
- 229920002643 polyglutamic acid Polymers 0.000 claims 1
- 229920000223 polyglycerol Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 1
- 239000001103 potassium chloride Substances 0.000 claims 1
- 235000011164 potassium chloride Nutrition 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
- 238000009210 therapy by ultrasound Methods 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
Applications Claiming Priority (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862627741P | 2018-02-07 | 2018-02-07 | |
| US201862627703P | 2018-02-07 | 2018-02-07 | |
| US62/627,741 | 2018-02-07 | ||
| US62/627,703 | 2018-02-07 | ||
| US201862630629P | 2018-02-14 | 2018-02-14 | |
| US62/630,629 | 2018-02-14 | ||
| US201862662374P | 2018-04-25 | 2018-04-25 | |
| US62/662,374 | 2018-04-25 | ||
| US201862702561P | 2018-07-24 | 2018-07-24 | |
| US201862702732P | 2018-07-24 | 2018-07-24 | |
| US62/702,732 | 2018-07-24 | ||
| US62/702,561 | 2018-07-24 | ||
| US201862764955P | 2018-08-17 | 2018-08-17 | |
| US201862764943P | 2018-08-17 | 2018-08-17 | |
| US62/764,943 | 2018-08-17 | ||
| US62/764,955 | 2018-08-17 | ||
| PCT/US2019/016989 WO2019157138A1 (en) | 2018-02-07 | 2019-02-07 | Alpha polyglutamated pemetrexed and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021512895A JP2021512895A (ja) | 2021-05-20 |
| JPWO2019157138A5 true JPWO2019157138A5 (de) | 2022-02-16 |
| JP7491572B2 JP7491572B2 (ja) | 2024-05-28 |
Family
ID=67549083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020542562A Active JP7491572B2 (ja) | 2018-02-07 | 2019-02-07 | アルファポリグルタミン酸化ペメトレキセドおよびその使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US11779584B2 (de) |
| EP (1) | EP3749317A4 (de) |
| JP (1) | JP7491572B2 (de) |
| CN (1) | CN111954531A (de) |
| CA (1) | CA3090494A1 (de) |
| WO (1) | WO2019157138A1 (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180236098A1 (en) | 2016-08-12 | 2018-08-23 | L.E.A.F. Holdings Group Llc | Alpha and gamma-d polyglutamated antifolates and uses thereof |
| CN109689104A (zh) | 2016-08-12 | 2019-04-26 | L.E.A.F.控股集团公司 | α和γ-D聚谷氨酸化抗叶酸剂及其用途 |
| CN111954531A (zh) | 2018-02-07 | 2020-11-17 | L.E.A.F.控股集团公司 | α聚谷氨酸化培美曲塞及其用途 |
| US20210052592A1 (en) * | 2018-02-07 | 2021-02-25 | L.E.A.F. Holdings Group Llc | Alpha polyglutamated aminopterin and uses thereof |
| JP7487107B2 (ja) | 2018-02-07 | 2024-05-20 | エル．イー．エー．エフ． ホールディングス グループ エルエルシー | アルファポリグルタミン酸化葉酸代謝拮抗薬およびその使用 |
| JP7490240B2 (ja) * | 2018-02-07 | 2024-05-27 | エル．イー．エー．エフ． ホールディングス グループ エルエルシー | ガンマポリグルタミン酸化葉酸代謝拮抗薬およびその使用 |
| US11730738B2 (en) | 2018-02-07 | 2023-08-22 | L.E.A.F. Holdings Group Llc | Alpha polyglutamated pralatrexate and uses thereof |
| WO2019160732A1 (en) * | 2018-02-14 | 2019-08-22 | L.E.A.F. Holdings Group Llc | Gamma polyglutamated aminopterin and uses thereof |
| EP3752157A4 (de) | 2018-02-14 | 2022-07-06 | L.E.A.F Holdings Group LLC | Gamma-polyglutamatiertes lometrexol und verwendungen davon |
| CN114539353A (zh) * | 2020-11-26 | 2022-05-27 | 南京碳硅人工智能生物医药技术研究院有限公司 | 培美曲塞多谷氨酸化代谢物及其制备方法 |
| WO2022119531A1 (en) * | 2020-12-01 | 2022-06-09 | Ege Üni̇versi̇tesi̇ | Investigation of the potential of pemetrexed-loaded liposome system in cancer treatment |
Family Cites Families (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4584375A (en) | 1984-08-21 | 1986-04-22 | Rensselaer Polytechnic Institute | Fluorine-containing antifolates incapable of polyglutamate formation |
| CA2057635A1 (en) | 1990-12-14 | 1992-06-15 | Hiroshi Akimoto | Condensed heterocyclic compounds, their production and use |
| US5646253A (en) | 1994-03-08 | 1997-07-08 | Memorial Sloan-Kettering Cancer Center | Recombinant human anti-LK26 antibodies |
| US6569432B1 (en) | 1995-02-24 | 2003-05-27 | Sloan-Kettering Institute For Cancer Research | Prostate-specific membrane antigen and uses thereof |
| DK0877563T3 (da) | 1996-01-31 | 2004-07-26 | Univ South Alabama | Levnedsmiddel- og vitaminpræparater, der indeholder den naturlige isomer af reducerede folater |
| US20020168761A1 (en) | 2000-01-24 | 2002-11-14 | Gour Barbara J. | Peptidomimetic modulators of cell adhesion |
| US5912251A (en) | 1998-01-17 | 1999-06-15 | Nair; Madhavan G. | Metabolically inert anti-inflammatory and anti-tumor antifolates |
| US20050031679A1 (en) | 1998-03-27 | 2005-02-10 | Clemens Unger | Method for producing liposomal formulations of active ingredients |
| BR9911935A (pt) | 1998-07-09 | 2001-04-03 | Rhodia Chimie Sa | Copolìmeros enxertados solúveis em água ou dispersáveis em água |
| WO2001005405A1 (en) | 1999-07-16 | 2001-01-25 | The General Hospital Corporation | Folylpolyglutamyl synthetase gene transfer to enhance antifolate drug sensitivity |
| CN1095472C (zh) | 2000-04-17 | 2002-12-04 | 上海复康医药科技发展有限公司 | 叶酸－多聚糖复合物，其制备方法和以该复合物为活性成分的药物组合物 |
| NZ522842A (en) | 2000-06-09 | 2004-11-26 | Osi Pharm Inc | Liposomal benzoquinazoline thymidylate synthase inhibitor formulations |
| ATE359823T1 (de) | 2000-06-30 | 2007-05-15 | Lilly Co Eli | Zusammensetzung, welche ein antifolate und ein methylmalonsäuresenkendes mittel enthält |
| CH696628A5 (de) | 2002-02-26 | 2007-08-31 | Eprova Ag | Verwendung von Folaten zur Herstellung einer Zubereitung geeignet zur Vorbeugung und Behandlung von Entzündungen und entzündungsassoziierter Krankheiten, im Speziellen zur Beeinflussung der |
| US7563590B2 (en) * | 2002-08-30 | 2009-07-21 | Cypress Bioscience Inc. | Methods of quantifying methotrexate metabolites |
| US6921667B2 (en) | 2003-03-07 | 2005-07-26 | Prometheus Laboratories, Inc. | Methods for direct detection of individual methotrexate metabolites |
| WO2005070465A2 (en) | 2004-01-14 | 2005-08-04 | Gilead Sciences, Inc. | Lipid-based dispersions useful for drug delivery |
| CA2556027C (en) | 2004-02-12 | 2015-11-24 | Morphotek, Inc. | Monoclonal antibodies that specifically block biological activity of a tumor antigen |
| US7612071B2 (en) | 2004-03-12 | 2009-11-03 | Syntrix Biosystems, Inc. | Compositions and methods employing aminopterin |
| US20080260812A1 (en) | 2004-04-26 | 2008-10-23 | Takami Matsuyama C/O Kagoshima University | Therapeutic Medicine Containing Monoclonal Antibody Against Folate Receptor Beta (Fr-Beta) |
| CN107811971B (zh) | 2004-05-03 | 2021-10-29 | 益普生生物制药公司 | 用于药物输送的脂质体 |
| US7695908B2 (en) | 2004-06-15 | 2010-04-13 | Prometheus Laboratories Inc. | Methods for predicting methotrexate polyglutamate levels using pharmacogenetics |
| WO2006029385A2 (en) * | 2004-09-08 | 2006-03-16 | Chelsea Therapeutics, Inc. | Quinazoline derivatives as metabolically inert antifolate compounds. |
| CN101031305A (zh) | 2004-09-29 | 2007-09-05 | 兴和株式会社 | 类风湿性关节炎的预防和/或治疗药物 |
| US8126089B2 (en) | 2004-09-30 | 2012-02-28 | Alcatel Lucent | Method and apparatus for providing frame synchronization in a digital communication system that supports multiple modulation formats |
| US20100266709A1 (en) | 2004-12-16 | 2010-10-21 | Hicks Terry Lee | Compositions and Methods for Treating Burns |
| WO2006074416A1 (en) | 2005-01-07 | 2006-07-13 | Health Research Inc. | 5-amino-4-imidazolecarboxamide riboside and its nucleobase as potentiators of antifolate transport and metabolism |
| JP2006248978A (ja) | 2005-03-10 | 2006-09-21 | Mebiopharm Co Ltd | 新規なリポソーム製剤 |
| EP1917027A2 (de) | 2005-08-24 | 2008-05-07 | Protherics Medicines Development Limited | Spaltung von anti-folat-verbindungen |
| WO2007066335A2 (en) | 2005-12-08 | 2007-06-14 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Methods for affecting liposome composition by ultrasound irradiation |
| WO2007098089A2 (en) | 2006-02-17 | 2007-08-30 | Novacea, Inc. | Treatment of hyperproliferative diseases with methotrexate n-oxide and analogs |
| US9265746B2 (en) | 2006-05-31 | 2016-02-23 | Merck & Cie | Method for cell-specific targeting |
| WO2008030818A2 (en) | 2006-09-05 | 2008-03-13 | Mebiopharm Co., Ltd. | Novel liposome compositions |
| RU2423114C2 (ru) | 2006-12-29 | 2011-07-10 | Тракон Фармасьютикалз, Инк. | Комбинации антифолатного агента в лечении рака |
| CN101652366A (zh) | 2007-01-19 | 2010-02-17 | 切尔西治疗公司 | 新型抗叶酸剂 |
| WO2009115776A1 (en) | 2008-03-18 | 2009-09-24 | Btg International Limited | Cyclopenta[g]quinazoline derivatives for the treatment of rheumatoid arthritis or acute myeloid leukaemia |
| GB0811360D0 (en) | 2008-06-20 | 2008-07-30 | Imp Innovations Ltd | Methods |
| US8609642B2 (en) * | 2009-06-03 | 2013-12-17 | Ex-Tek, Llc | Skin treatment compositions |
| TW201118098A (en) | 2009-08-13 | 2011-06-01 | Reddy S Lab Liimited Dr | Processes for preparing pemetrexed |
| NZ724971A (en) | 2010-02-24 | 2019-06-28 | Immunogen Inc | Folate receptor 1 antibodies and immunoconjugates and uses thereof |
| WO2011115684A2 (en) | 2010-03-19 | 2011-09-22 | Massachusetts Institute Of Technology | Lipid vesicle compositions and methods of use |
| US9770414B2 (en) | 2010-05-13 | 2017-09-26 | Pacira Pharmaceuticals, Inc. | Sustained release formulation of methotrexate as a disease-modifying antirheumatic drug (DMARD) and an anti-cancer agent |
| EP2394640A1 (de) | 2010-05-21 | 2011-12-14 | MediGene AG | Verbesserte liposomale Formulierungen von lipophilen Verbindungen |
| WO2011150392A1 (en) | 2010-05-28 | 2011-12-01 | Purdue Research Foundation | Delivery of therapeutic agents to inflamed tissues using folate-targeted agents |
| WO2012033987A2 (en) | 2010-09-09 | 2012-03-15 | Purdue Research Foundation | Anti-human folate receptor beta antibodies and methods of use |
| US9261509B2 (en) | 2010-09-13 | 2016-02-16 | Thierry Dervieux | Methods for monitoring methotrexate therapy |
| KR101931936B1 (ko) | 2010-11-05 | 2018-12-26 | 에이자이 아이엔씨. | 엽산 수용체 알파-발현 암에 대한 진단 및 예후 마커로서의 엽산 수용체 알파 |
| WO2012078708A1 (en) * | 2010-12-07 | 2012-06-14 | Chelsea Therapeutics, Inc. | Combination comprising methotrexate and an antifolate compound |
| WO2012118806A2 (en) | 2011-02-28 | 2012-09-07 | The Regents Of The University Of California | Compositions and methods for detecting and treating cancer |
| WO2012121682A2 (en) | 2011-03-10 | 2012-09-13 | National Science And Technology Development Agency | Anti-folate antimalarials with dual-binding modes and their preparation |
| US8183227B1 (en) | 2011-07-07 | 2012-05-22 | Chemo S. A. France | Compositions, kits and methods for nutrition supplementation |
| PL2731591T3 (pl) | 2011-07-13 | 2021-05-17 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Liposomy zawierające bisfosfonian i środek amfipatyczny w wyniku ko-enkapsulacji |
| SG10201605278PA (en) | 2011-07-15 | 2016-08-30 | Eisai R&D Man Co Ltd | Anti-folate receptor alpha antibodies and uses thereof |
| EP2591770B1 (de) | 2011-11-14 | 2016-03-16 | Silenseed Ltd | Zusammensetzungen zur siRNA-Freisetzung und Verfahren zu ihrer Herstellung und Verwendung |
| WO2014003137A1 (ja) | 2012-06-27 | 2014-01-03 | 旭化成メディカル株式会社 | 高アフィニティー抗体、及びその製造方法 |
| US9440979B2 (en) | 2012-07-23 | 2016-09-13 | Fresenius Kabi Oncology Limited | Process for the preparation of pralatrexate |
| US20140120157A1 (en) | 2012-09-19 | 2014-05-01 | Georgetown University | Targeted liposomes |
| WO2014046630A1 (en) | 2012-09-19 | 2014-03-27 | Keskin, Dilek | Tumor targeted liposomal drug delivery system |
| AU2013355931B2 (en) | 2012-12-07 | 2019-03-14 | Kyowa Kirin Co., Ltd. | Anti-FOLR1 antibody |
| CN103040748B (zh) | 2012-12-18 | 2014-07-02 | 海南圣欣医药科技有限公司 | 一种培美曲塞二钠脂质体注射剂 |
| CN105308072A (zh) | 2013-05-14 | 2016-02-03 | 伊缪诺金公司 | 抗folr1免疫缀合物给药方案 |
| ES2905498T3 (es) * | 2014-08-14 | 2022-04-08 | L E A F Holdings Group Llc | Medicamento con afinidad encapsulado en liposoma |
| KR20190003630A (ko) | 2016-04-29 | 2019-01-09 | 메모리얼 슬로안 케터링 캔서 센터 | 악성 뇌 종양에서의 표적화된 입자 침투, 분포, 및 반응을 위한 조성물 및 방법 |
| US20180236098A1 (en) * | 2016-08-12 | 2018-08-23 | L.E.A.F. Holdings Group Llc | Alpha and gamma-d polyglutamated antifolates and uses thereof |
| CN109689104A (zh) | 2016-08-12 | 2019-04-26 | L.E.A.F.控股集团公司 | α和γ-D聚谷氨酸化抗叶酸剂及其用途 |
| WO2018031979A1 (en) * | 2016-08-12 | 2018-02-15 | L.E.A.F. Holdings Group Llc | Alpha and gamma-d polyglutamated antifolates and uses thereof |
| EP3706801A4 (de) | 2017-11-08 | 2022-04-06 | L.E.A.F Holdings Group LLC | Platinkomplexe und verwendungen davon |
| CN111954531A (zh) | 2018-02-07 | 2020-11-17 | L.E.A.F.控股集团公司 | α聚谷氨酸化培美曲塞及其用途 |
| EP3749318A4 (de) | 2018-02-07 | 2022-07-06 | L.E.A.F Holdings Group LLC | Gamma-polyglutamiertes raltitrexed und dessen verwendungen |
| EP3749319A4 (de) | 2018-02-07 | 2022-06-22 | L.E.A.F Holdings Group LLC | Alpha-polyglutamierte tetrahydrofolate und verwendungen davon |
| WO2019157121A1 (en) | 2018-02-07 | 2019-08-15 | L.E.A.F. Holdings Group Llc | Alpha polyglutamated lometrexol and uses thereof |
| US20210052592A1 (en) | 2018-02-07 | 2021-02-25 | L.E.A.F. Holdings Group Llc | Alpha polyglutamated aminopterin and uses thereof |
| US20210169884A1 (en) | 2018-02-07 | 2021-06-10 | L.E.A.F. Holdings Group Llc | Alpha polyglutamated raltitrexed and uses thereof |
| JP7487107B2 (ja) | 2018-02-07 | 2024-05-20 | エル．イー．エー．エフ． ホールディングス グループ エルエルシー | アルファポリグルタミン酸化葉酸代謝拮抗薬およびその使用 |
| US20210161899A1 (en) | 2018-02-07 | 2021-06-03 | L.E.A.F. Holdings Group Llc | Gamma polyglutamated pemetrexed and uses thereof |
| JP7490240B2 (ja) | 2018-02-07 | 2024-05-27 | エル．イー．エー．エフ． ホールディングス グループ エルエルシー | ガンマポリグルタミン酸化葉酸代謝拮抗薬およびその使用 |
| CA3090509A1 (en) | 2018-02-07 | 2019-08-15 | L.E.A.F. Holdings Group Llc | Alpha polyglutamated methotrexate and uses thereof |
| US11730738B2 (en) | 2018-02-07 | 2023-08-22 | L.E.A.F. Holdings Group Llc | Alpha polyglutamated pralatrexate and uses thereof |
| EP3755335A4 (de) | 2018-02-14 | 2022-06-22 | L.E.A.F Holdings Group LLC | Gamma-polyglutamierte tetrahydrofolate und deren verwendungen |
| EP3752157A4 (de) | 2018-02-14 | 2022-07-06 | L.E.A.F Holdings Group LLC | Gamma-polyglutamatiertes lometrexol und verwendungen davon |
| WO2019160732A1 (en) | 2018-02-14 | 2019-08-22 | L.E.A.F. Holdings Group Llc | Gamma polyglutamated aminopterin and uses thereof |
| US20210154196A1 (en) | 2018-02-14 | 2021-05-27 | L.E.A.F. Holdings Group Llc | Gamma polyglutamated methotrexate and uses thereof |
| WO2019160736A1 (en) | 2018-02-14 | 2019-08-22 | L.E.A.F. Holdings Group Llc | Gamma polyglutamated pralatrexate and uses thereof |
| US20230000997A1 (en) | 2019-08-06 | 2023-01-05 | L.E.A.F. Holdings Group Llc | Processes of preparing polyglutamated antifolates and uses of their compositions |
-
2019
- 2019-02-07 CN CN201980024908.7A patent/CN111954531A/zh active Pending
- 2019-02-07 CA CA3090494A patent/CA3090494A1/en active Pending
- 2019-02-07 US US16/967,212 patent/US11779584B2/en active Active
- 2019-02-07 JP JP2020542562A patent/JP7491572B2/ja active Active
- 2019-02-07 WO PCT/US2019/016989 patent/WO2019157138A1/en unknown
- 2019-02-07 EP EP19751234.6A patent/EP3749317A4/de active Pending
-
2023
- 2023-06-01 US US18/204,566 patent/US20240173321A1/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019524885A5 (de) | ||
| JP2019524802A5 (de) | ||
| JP2017526744A5 (de) | ||
| US20210393806A1 (en) | Cross-linked polymer modified nanoparticles | |
| Wu et al. | Reversing of multidrug resistance breast cancer by co-delivery of P-gp siRNA and doxorubicin via folic acid-modified core-shell nanomicelles | |
| Kierstead et al. | The effect of polymer backbone chemistry on the induction of the accelerated blood clearance in polymer modified liposomes | |
| JPWO2019157138A5 (de) | ||
| AU2011353233B2 (en) | Carrier for negatively charged drugs comprising a cationic lipid and a preparation method thereof | |
| US11241494B2 (en) | Method for eliciting an immune response to an immunogen | |
| WO2017041033A1 (en) | Mesoporous silica nanoparticles and supported lipid bi-layer nanoparticles for biomedical applications | |
| Dancy et al. | Non-specific binding and steric hindrance thresholds for penetration of particulate drug carriers within tumor tissue | |
| JP5692887B1 (ja) | ポリマーミセル医薬組成物 | |
| JPWO2019157145A5 (de) | ||
| WO2015082080A1 (en) | Means for lung specific delivery | |
| US20150125401A1 (en) | Small magnetite therapeutics and methods of use thereof | |
| JPWO2019157125A5 (de) | ||
| WO2016083336A1 (en) | Pharmaceutical composition, preparation and uses thereof | |
| JPWO2019157146A5 (de) | ||
| Zhang et al. | Distinctive polymer micelle designed for siRNA delivery and reversal of MDR1 gene‐dependent multidrug resistance | |
| JPWO2019160733A5 (de) | ||
| JPWO2019157120A5 (de) | ||
| JPWO2019160735A5 (de) | ||
| JP5787323B2 (ja) | 脂質膜構造体 | |
| Safaei et al. | Enzyme-sensitive nanoparticles, smart TAT and cetuximab conjugated immunoliposomes to overcome multidrug resistance in breast cancer cells | |
| JPWO2019157148A5 (de) |