JP2020507584A5 - - Google Patents
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- JP2020507584A5 JP2020507584A5 JP2019543387A JP2019543387A JP2020507584A5 JP 2020507584 A5 JP2020507584 A5 JP 2020507584A5 JP 2019543387 A JP2019543387 A JP 2019543387A JP 2019543387 A JP2019543387 A JP 2019543387A JP 2020507584 A5 JP2020507584 A5 JP 2020507584A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound according
- formula
- amino
- pharmaceutically acceptable
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 162
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000005647 linker group Chemical group 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 39
- -1 2-Amino-2-deoxy-D-galactopyranosyl moiety Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000001475 halogen functional group Chemical group 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 18
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 108010038807 Oligopeptides Chemical group 0.000 claims description 10
- 102000015636 Oligopeptides Human genes 0.000 claims description 10
- 150000001413 amino acids Chemical group 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000002519 galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims description 8
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 8
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 230000003211 malignant effect Effects 0.000 claims description 6
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003923 2,5-pyrrolediones Chemical group 0.000 claims description 2
- 150000002019 disulfides Chemical group 0.000 claims description 2
- 150000002148 esters Chemical group 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 150000003568 thioethers Chemical group 0.000 claims description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 12
- 238000003776 cleavage reaction Methods 0.000 description 10
- 230000007017 scission Effects 0.000 description 10
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- 108010084457 Cathepsins Proteins 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 5
- 239000002246 antineoplastic agent Substances 0.000 description 5
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- 101710088194 Dehydrogenase Proteins 0.000 description 4
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- 206010021143 Hypoxia Diseases 0.000 description 4
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 4
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 150000004053 quinones Chemical class 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 150000007944 thiolates Chemical class 0.000 description 4
- AGGWFDNPHKLBBV-YUMQZZPRSA-N (2s)-2-[[(2s)-2-amino-3-methylbutanoyl]amino]-5-(carbamoylamino)pentanoic acid Chemical compound CC(C)[C@H](N)C(=O)N[C@H](C(O)=O)CCCNC(N)=O AGGWFDNPHKLBBV-YUMQZZPRSA-N 0.000 description 3
- 0 C*C(C1(CCCCC(C2)C*2C(C)(C)CCC(C2)[C@@]2C(C)(C)C)[C@](C)C1)C(N)=C Chemical compound C*C(C1(CCCCC(C2)C*2C(C)(C)CCC(C2)[C@@]2C(C)(C)C)[C@](C)C1)C(N)=C 0.000 description 3
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical group [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 2
- QXRNAOYBCYVZCD-BQBZGAKWSA-N Ala-Lys Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CCCCN QXRNAOYBCYVZCD-BQBZGAKWSA-N 0.000 description 2
- OLDXRTOEUPVZKB-UHFFFAOYSA-N B1CCCC1 Chemical group B1CCCC1 OLDXRTOEUPVZKB-UHFFFAOYSA-N 0.000 description 2
- ZUHQCDZJPTXVCU-UHFFFAOYSA-N C1#CCCC2=CC=CC=C2C2=CC=CC=C21 Chemical group C1#CCCC2=CC=CC=C2C2=CC=CC=C21 ZUHQCDZJPTXVCU-UHFFFAOYSA-N 0.000 description 2
- 102000004172 Cathepsin L Human genes 0.000 description 2
- 108090000624 Cathepsin L Proteins 0.000 description 2
- 108010092160 Dactinomycin Proteins 0.000 description 2
- 108010024636 Glutathione Proteins 0.000 description 2
- HKXLAGBDJVHRQG-YFKPBYRVSA-N L-lysinamide Chemical class NCCCC[C@H](N)C(N)=O HKXLAGBDJVHRQG-YFKPBYRVSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- OZILORBBPKKGRI-RYUDHWBXSA-N Phe-Arg Chemical compound NC(N)=NCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CC=CC=C1 OZILORBBPKKGRI-RYUDHWBXSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JKHXYJKMNSSFFL-IUCAKERBSA-N Val-Lys Chemical compound CC(C)[C@H](N)C(=O)N[C@H](C(O)=O)CCCCN JKHXYJKMNSSFFL-IUCAKERBSA-N 0.000 description 2
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 2
- 229960002932 anastrozole Drugs 0.000 description 2
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 2
- 125000005621 boronate group Chemical group 0.000 description 2
- 125000005620 boronic acid group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
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- 229960004679 doxorubicin Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229960003180 glutathione Drugs 0.000 description 2
- 125000003827 glycol group Chemical group 0.000 description 2
- 230000007954 hypoxia Effects 0.000 description 2
- 230000001146 hypoxic effect Effects 0.000 description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 229960001592 paclitaxel Drugs 0.000 description 2
- 108010018625 phenylalanylarginine Proteins 0.000 description 2
- 229960003604 testosterone Drugs 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 108010073969 valyllysine Proteins 0.000 description 2
- FWPWHHUJACGNMZ-NBBQQVJHSA-N (1s,2r,5r)-5-[(1s)-1-hydroxy-2-methylpropyl]-2-methyl-7-oxa-4-azabicyclo[3.2.0]heptane-3,6-dione Chemical compound N1C(=O)[C@H](C)[C@@H]2OC(=O)[C@@]21[C@@H](O)C(C)C FWPWHHUJACGNMZ-NBBQQVJHSA-N 0.000 description 1
- DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 description 1
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 1
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 description 1
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
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- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
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| CN118603851A (zh) * | 2024-05-22 | 2024-09-06 | 杭州瑞奥生物医药有限公司 | 一种检测细胞表面叠氮的两步法荧光标记流式方法及其应用 |
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| DK1102785T3 (da) * | 1999-06-07 | 2013-05-13 | Arrowhead Res Corp | Sammensætninger til lægemiddeltilførsel ved anvendelse af pH-følsomme molekyler |
| LT1912671T (lt) * | 2005-07-18 | 2017-12-11 | Seattle Genetics, Inc. | Vaisto konjugatai, turintys gliukoronido linkerį |
| EP2877480B1 (en) * | 2012-06-28 | 2017-09-06 | Universiteit Gent | Galactopyranosyl derivatives useful as medicaments |
| CN105142672B (zh) | 2012-10-23 | 2019-04-05 | 西纳福克斯股份有限公司 | 经修饰的抗体、抗体-缀合物及其制备方法 |
| WO2014085275A1 (en) * | 2012-11-30 | 2014-06-05 | University Of Massachusetts Medical School | Multi-functional surface coating of implants |
| AU2013364065B2 (en) | 2012-12-21 | 2018-10-04 | Altrubio Inc. | Hydrophilic self-immolative linkers and conjugates thereof |
| US9695189B2 (en) | 2013-03-01 | 2017-07-04 | Mark Quang Nguyen | Chemical crosslinkers and compositions thereof |
| ES2865473T3 (es) | 2013-07-10 | 2021-10-15 | Sutro Biopharma Inc | Anticuerpos que comprenden múltiples residuos de aminoácidos no naturales sitio-específicos, métodos para su preparación y métodos de uso |
| WO2015021305A1 (en) | 2013-08-09 | 2015-02-12 | The Research Foundation For The State Univeristy Of New York | Cancer cell specific imaging probes and methods of use |
| US10550190B2 (en) * | 2014-04-04 | 2020-02-04 | Merck Sharp & Dohme Corp. | Phosphate based linkers for intracellular delivery of drug conjugates |
| CN107406463A (zh) * | 2014-12-04 | 2017-11-28 | 细胞基因公司 | 生物分子共轭物 |
| PL3250237T3 (pl) * | 2015-01-30 | 2021-12-13 | Sutro Biopharma, Inc. | Pochodne hemiasterliny do koniugacji i terapii |
| JP6892694B2 (ja) * | 2015-10-07 | 2021-06-23 | ザ ボード オブ トラスティーズ オブ ザ ユニヴァーシティ オブ イリノイＴｈｅ Ｂｏａｒｄ Ｏｆ Ｔｒｕｓｔｅｅｓ Ｏｆ Ｔｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｉｌｌｉｎｏｉｓ | 癌選択性標識化及び標的指向化のためのトリガー活性型代謝糖前駆体 |
| US11299509B2 (en) | 2017-02-10 | 2022-04-12 | The Board Of Trustees Of The University Of Illinois | Trigger-activatable sugar conjugates for cancer-selective labeling and targeting |
-
2018
- 2018-02-12 US US16/485,090 patent/US11299509B2/en active Active
- 2018-02-12 WO PCT/US2018/017802 patent/WO2018148650A1/en not_active Ceased
- 2018-02-12 KR KR1020197025795A patent/KR20190126314A/ko not_active Withdrawn
- 2018-02-12 EP EP18751686.9A patent/EP3595729A4/en not_active Withdrawn
- 2018-02-12 JP JP2019543387A patent/JP2020507584A/ja not_active Abandoned
- 2018-02-12 CN CN201880023821.3A patent/CN110520161A/zh active Pending
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