JPWO2019160735A5 - - Google Patents
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- Publication number
- JPWO2019160735A5 JPWO2019160735A5 JP2020543517A JP2020543517A JPWO2019160735A5 JP WO2019160735 A5 JPWO2019160735 A5 JP WO2019160735A5 JP 2020543517 A JP2020543517 A JP 2020543517A JP 2020543517 A JP2020543517 A JP 2020543517A JP WO2019160735 A5 JPWO2019160735 A5 JP WO2019160735A5
- Authority
- JP
- Japan
- Prior art keywords
- liposome
- acid
- group
- glutamil
- optionally
- 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.)
- Granted
Links
- 239000002502 liposome Substances 0.000 claims 33
- 239000000203 mixture Substances 0.000 claims 19
- MSTNYGQPCMXVAQ-KIYNQFGBSA-N 5,6,7,8-tetrahydrofolic acid Chemical compound N1C=2C(=O)NC(N)=NC=2NCC1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 MSTNYGQPCMXVAQ-KIYNQFGBSA-N 0.000 claims 16
- 229920002643 polyglutamic acid Polymers 0.000 claims 16
- 108010020346 Polyglutamic Acid Proteins 0.000 claims 14
- 230000003647 oxidation Effects 0.000 claims 13
- 238000007254 oxidation reaction Methods 0.000 claims 13
- 229920001223 polyethylene glycol Polymers 0.000 claims 11
- 230000008685 targeting Effects 0.000 claims 10
- 229920000155 polyglutamine Polymers 0.000 claims 9
- 239000002202 Polyethylene glycol Substances 0.000 claims 7
- 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 6
- 238000000034 method Methods 0.000 claims 6
- 102000006815 folate receptor Human genes 0.000 claims 5
- 108020005243 folate receptor Proteins 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 102000010449 Folate receptor beta Human genes 0.000 claims 4
- 108050001930 Folate receptor beta Proteins 0.000 claims 4
- 239000000839 emulsion Substances 0.000 claims 4
- 238000002156 mixing Methods 0.000 claims 4
- MSTNYGQPCMXVAQ-RYUDHWBXSA-N (6S)-5,6,7,8-tetrahydrofolic acid Chemical compound C([C@H]1CNC=2N=C(NC(=O)C=2N1)N)NC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 MSTNYGQPCMXVAQ-RYUDHWBXSA-N 0.000 claims 3
- 229920002498 Beta-glucan Polymers 0.000 claims 3
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 239000000427 antigen Substances 0.000 claims 3
- 102000036639 antigens Human genes 0.000 claims 3
- 108091007433 antigens Proteins 0.000 claims 3
- 235000012000 cholesterol Nutrition 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 238000001125 extrusion Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- -1 poroxummer 188 Polymers 0.000 claims 3
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims 2
- LVNGJLRDBYCPGB-LDLOPFEMSA-N (R)-1,2-distearoylphosphatidylethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCCCCCCCCCCCC LVNGJLRDBYCPGB-LDLOPFEMSA-N 0.000 claims 2
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 claims 2
- 238000010146 3D printing Methods 0.000 claims 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 2
- 102000010451 Folate receptor alpha Human genes 0.000 claims 2
- 108050001931 Folate receptor alpha Proteins 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 2
- 101001105486 Homo sapiens Proteasome subunit alpha type-7 Proteins 0.000 claims 2
- 229930195725 Mannitol Natural products 0.000 claims 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims 2
- 102100021201 Proteasome subunit alpha type-7 Human genes 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 102100023119 Sperm-egg fusion protein Juno Human genes 0.000 claims 2
- 101710093389 Sperm-egg fusion protein Juno Proteins 0.000 claims 2
- 102000002689 Toll-like receptor Human genes 0.000 claims 2
- 108020000411 Toll-like receptor Proteins 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
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-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
- 125000000129 anionic group Chemical group 0.000 claims 2
- 210000004899 c-terminal region Anatomy 0.000 claims 2
- 239000008121 dextrose Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 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 2
- 238000001704 evaporation Methods 0.000 claims 2
- 229960002949 fluorouracil Drugs 0.000 claims 2
- 230000036571 hydration Effects 0.000 claims 2
- 238000006703 hydration reaction Methods 0.000 claims 2
- 229960001438 immunostimulant agent Drugs 0.000 claims 2
- 239000003022 immunostimulating agent Substances 0.000 claims 2
- 230000003308 immunostimulating effect Effects 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
- 230000007935 neutral effect Effects 0.000 claims 2
- 229920000729 poly(L-lysine) polymer Polymers 0.000 claims 2
- 229920002401 polyacrylamide Polymers 0.000 claims 2
- 108010040003 polyglutamine Proteins 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 239000005460 tetrahydrofolate Substances 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 239000010409 thin film Substances 0.000 claims 2
- FYGDTMLNYKFZSV-URKRLVJHSA-N (2s,3r,4s,5s,6r)-2-[(2r,4r,5r,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,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](OC2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-URKRLVJHSA-N 0.000 claims 1
- QYNUQALWYRSVHF-OLZOCXBDSA-N (6R)-5,10-methylenetetrahydrofolic acid Chemical compound C([C@H]1CNC=2N=C(NC(=O)C=2N1C1)N)N1C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 QYNUQALWYRSVHF-OLZOCXBDSA-N 0.000 claims 1
- ZNOVTXRBGFNYRX-STQMWFEESA-N (6S)-5-methyltetrahydrofolic acid Chemical compound C([C@@H]1N(C=2C(=O)N=C(N)NC=2NC1)C)NC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 ZNOVTXRBGFNYRX-STQMWFEESA-N 0.000 claims 1
- AUFGTPPARQZWDO-YPMHNXCESA-N 10-formyltetrahydrofolic acid Chemical compound C([C@H]1CNC=2N=C(NC(=O)C=2N1)N)N(C=O)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 AUFGTPPARQZWDO-YPMHNXCESA-N 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
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 claims 1
- MEANFMOQMXYMCT-OLZOCXBDSA-N 5,10-methenyltetrahydrofolic acid Chemical compound C([C@H]1CNC2=C([N+]1=C1)C(=O)N=C(N2)N)N1C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C([O-])=O)C=C1 MEANFMOQMXYMCT-OLZOCXBDSA-N 0.000 claims 1
- ZNOVTXRBGFNYRX-ZGTCLIOFSA-N 5-methyltetrahydrofolic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C)C1CNC1=CC=C(C(=O)N[C@H](CCC(O)=O)C(O)=O)C=C1 ZNOVTXRBGFNYRX-ZGTCLIOFSA-N 0.000 claims 1
- VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 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
- 239000007995 HEPES buffer Substances 0.000 claims 1
- 150000008575 L-amino acids Chemical class 0.000 claims 1
- OHXXUCPXGUBFNL-KIYNQFGBSA-N NC(NC1=O)=NC2=C1NC(CNC(C=C1)=CC=C1C(N([C@@H](CCC(O)=O)C(O)=O)O)=O)CN2 Chemical compound NC(NC1=O)=NC2=C1NC(CNC(C=C1)=CC=C1C(N([C@@H](CCC(O)=O)C(O)=O)O)=O)CN2 OHXXUCPXGUBFNL-KIYNQFGBSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 1
- 108010003723 Single-Domain Antibodies Proteins 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N 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
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229920006187 aquazol Polymers 0.000 claims 1
- 239000012861 aquazol Substances 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-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
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 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
- 201000011510 cancer Diseases 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 239000002577 cryoprotective agent Substances 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 238000010494 dissociation reaction Methods 0.000 claims 1
- 230000005593 dissociations Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 238000005516 engineering process Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical group O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000012634 fragment Substances 0.000 claims 1
- 238000004108 freeze drying Methods 0.000 claims 1
- 238000007710 freezing Methods 0.000 claims 1
- 230000008014 freezing Effects 0.000 claims 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 238000001802 infusion Methods 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 239000007951 isotonicity adjuster Substances 0.000 claims 1
- 210000000265 leukocyte Anatomy 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 108010071584 oxidized low density lipoprotein Proteins 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
- 229920002187 poly[N-2-(hydroxypropyl) methacrylamide] polymer Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 229920001451 polypropylene glycol 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
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
- 238000009210 therapy by ultrasound Methods 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024020715A JP2024056882A (ja) | 2018-02-14 | 2024-02-14 | γポリグルタミン酸化テトラヒドロ葉酸およびその使用 |
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862630824P | 2018-02-14 | 2018-02-14 | |
| US62/630,824 | 2018-02-14 | ||
| US201862636289P | 2018-02-28 | 2018-02-28 | |
| US62/636,289 | 2018-02-28 | ||
| US201862662372P | 2018-04-25 | 2018-04-25 | |
| US62/662,372 | 2018-04-25 | ||
| US201862702774P | 2018-07-24 | 2018-07-24 | |
| US62/702,774 | 2018-07-24 | ||
| US201862764945P | 2018-08-17 | 2018-08-17 | |
| US62/764,945 | 2018-08-17 | ||
| PCT/US2019/016966 WO2019160735A1 (en) | 2018-02-14 | 2019-02-07 | Gamma polyglutamated tetrahydrofolates and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024020715A Division JP2024056882A (ja) | 2018-02-14 | 2024-02-14 | γポリグルタミン酸化テトラヒドロ葉酸およびその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021513550A JP2021513550A (ja) | 2021-05-27 |
| JPWO2019160735A5 true JPWO2019160735A5 (de) | 2022-03-03 |
| JP7442822B2 JP7442822B2 (ja) | 2024-03-05 |
Family
ID=67618810
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020543517A Active JP7442822B2 (ja) | 2018-02-14 | 2019-02-07 | γポリグルタミン酸化テトラヒドロ葉酸およびその使用 |
| JP2024020715A Pending JP2024056882A (ja) | 2018-02-14 | 2024-02-14 | γポリグルタミン酸化テトラヒドロ葉酸およびその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024020715A Pending JP2024056882A (ja) | 2018-02-14 | 2024-02-14 | γポリグルタミン酸化テトラヒドロ葉酸およびその使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US12048766B2 (de) |
| EP (1) | EP3755335A4 (de) |
| JP (2) | JP7442822B2 (de) |
| CN (1) | CN111971047A (de) |
| CA (1) | CA3090992A1 (de) |
| WO (1) | WO2019160735A1 (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018031967A1 (en) | 2016-08-12 | 2018-02-15 | L.E.A.F. Holdings Group Llc | 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 |
| WO2019157148A1 (en) * | 2018-02-07 | 2019-08-15 | L.E.A.F. Holdings Group Llc | Gamma polyglutamated antifolates and uses thereof |
| 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 |
| EP3749313A4 (de) | 2018-02-07 | 2022-03-16 | L.E.A.F Holdings Group LLC | Alpha-polyglutamatierte antifolate und verwendungen davon |
| 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 |
| CN111936146A (zh) * | 2018-02-07 | 2020-11-13 | L.E.A.F.控股集团公司 | α聚谷氨酸化四氢叶酸及其用途 |
| WO2019160736A1 (en) | 2018-02-14 | 2019-08-22 | L.E.A.F. Holdings Group Llc | Gamma polyglutamated pralatrexate and uses thereof |
| CA3090943A1 (en) * | 2018-02-14 | 2019-08-22 | L.E.A.F. Holdings Group Llc | Gamma polyglutamated aminopterin and uses thereof |
| CN111971047A (zh) | 2018-02-14 | 2020-11-20 | L.E.A.F.控股集团公司 | γ聚谷氨酸化四氢叶酸及其用途 |
| EP3752157A4 (de) | 2018-02-14 | 2022-07-06 | L.E.A.F Holdings Group LLC | Gamma-polyglutamatiertes lometrexol und verwendungen davon |
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| FR2564319A1 (fr) | 1984-05-21 | 1985-11-22 | Inst Nat Sante Rech Med | Nouvelles compositions de liposomes dotees d'une action specifique vis-a-vis de la proliferation de cellules donnees |
| 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 |
| DE69728379T2 (de) | 1996-01-31 | 2005-02-24 | South Alabama Medical Science Foundation, Mobile | Lebensmittel und vitamin herstellungen mit natürlichem isomeren von reduzierten folaten |
| 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 |
| CN1239545C (zh) | 1998-07-09 | 2006-02-01 | 罗狄亚化学公司 | 水溶性或水可分散性接枝共聚物 |
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2019
- 2019-02-07 CN CN201980024858.2A patent/CN111971047A/zh active Pending
- 2019-02-07 CA CA3090992A patent/CA3090992A1/en active Pending
- 2019-02-07 WO PCT/US2019/016966 patent/WO2019160735A1/en unknown
- 2019-02-07 EP EP19754705.2A patent/EP3755335A4/de active Pending
- 2019-02-07 US US16/967,203 patent/US12048766B2/en active Active
- 2019-02-07 JP JP2020543517A patent/JP7442822B2/ja active Active
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2024
- 2024-02-14 JP JP2024020715A patent/JP2024056882A/ja active Pending
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