JP2017506628A5 - - Google Patents
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- JP2017506628A5 JP2017506628A5 JP2016550736A JP2016550736A JP2017506628A5 JP 2017506628 A5 JP2017506628 A5 JP 2017506628A5 JP 2016550736 A JP2016550736 A JP 2016550736A JP 2016550736 A JP2016550736 A JP 2016550736A JP 2017506628 A5 JP2017506628 A5 JP 2017506628A5
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- JP
- Japan
- Prior art keywords
- group
- conjugate according
- prodrug
- represent
- functional group
- 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.)
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- 239000000651 prodrug Substances 0.000 claims description 17
- 229940002612 prodrug Drugs 0.000 claims description 17
- 125000000524 functional group Chemical group 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 150000003573 thiols Chemical group 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- 102000009027 Albumins Human genes 0.000 claims description 7
- 108010088751 Albumins Proteins 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 108010093470 monomethyl auristatin E Proteins 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- IEDXPSOJFSVCKU-HOKPPMCLSA-N [4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[6-(2,5-dioxopyrrolidin-1-yl)hexanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methyl N-[(2S)-1-[[(2S)-1-[[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]-N-methylcarbamate Chemical compound CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@H](C)[C@@H](O)c1ccccc1)OC)N(C)C(=O)[C@@H](NC(=O)[C@H](C(C)C)N(C)C(=O)OCc1ccc(NC(=O)[C@H](CCCNC(N)=O)NC(=O)[C@@H](NC(=O)CCCCCN2C(=O)CCC2=O)C(C)C)cc1)C(C)C IEDXPSOJFSVCKU-HOKPPMCLSA-N 0.000 claims description 4
- WOWDZACBATWTAU-FEFUEGSOSA-N (2s)-2-[[(2s)-2-(dimethylamino)-3-methylbutanoyl]amino]-n-[(3r,4s,5s)-1-[(2s)-2-[(1r,2r)-3-[[(1s,2r)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-n,3-dimethylbutanamide Chemical compound CC(C)[C@H](N(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)[C@H](OC)CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@H](C)[C@@H](O)C1=CC=CC=C1 WOWDZACBATWTAU-FEFUEGSOSA-N 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- OFDNQWIFNXBECV-UHFFFAOYSA-N Dolastatin 10 Natural products CC(C)C(N(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(C(C)CC)C(OC)CC(=O)N1CCCC1C(OC)C(C)C(=O)NC(C=1SC=CN=1)CC1=CC=CC=C1 OFDNQWIFNXBECV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 235000001014 amino acid Nutrition 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- AMRJKAQTDDKMCE-UHFFFAOYSA-N dolastatin Chemical compound CC(C)C(N(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(C(C)C)C(OC)CC(=O)N1CCCC1C(OC)C(C)C(=O)NC(C=1SC=CN=1)CC1=CC=CC=C1 AMRJKAQTDDKMCE-UHFFFAOYSA-N 0.000 claims description 2
- 229930188854 dolastatin Natural products 0.000 claims description 2
- OFDNQWIFNXBECV-VFSYNPLYSA-N dolastatin 10 Chemical compound CC(C)[C@H](N(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)[C@H](OC)CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@H](C=1SC=CN=1)CC1=CC=CC=C1 OFDNQWIFNXBECV-VFSYNPLYSA-N 0.000 claims description 2
- 108010045524 dolastatin 10 Proteins 0.000 claims description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 239000012634 fragment Substances 0.000 claims description 2
- 125000003147 glycosyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 229920002521 macromolecule Polymers 0.000 claims description 2
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 108010047846 soblidotin Proteins 0.000 claims description 2
- DZMVCVHATYROOS-ZBFGKEHZSA-N soblidotin Chemical compound CC(C)[C@H](N(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)[C@H](OC)CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)NCCC1=CC=CC=C1 DZMVCVHATYROOS-ZBFGKEHZSA-N 0.000 claims description 2
- 125000006850 spacer group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- DJQYYYCQOZMCRC-UHFFFAOYSA-N 2-aminopropane-1,3-dithiol Chemical group SCC(N)CS DJQYYYCQOZMCRC-UHFFFAOYSA-N 0.000 claims 1
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical class O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- -1 monomethylauristatin E glucuronide Chemical class 0.000 description 3
- 102000053187 Glucuronidase Human genes 0.000 description 2
- 108010060309 Glucuronidase Proteins 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 102000005936 beta-Galactosidase Human genes 0.000 description 1
- 108010005774 beta-Galactosidase Proteins 0.000 description 1
- 238000012925 biological evaluation Methods 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930182480 glucuronide Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1450956 | 2014-02-07 | ||
| FR1450956A FR3017298B1 (fr) | 2014-02-07 | 2014-02-07 | Conjugues et pro-drogues pour le traitement du cancer et de maladies inflammatoires |
| PCT/IB2015/050914 WO2015118497A1 (fr) | 2014-02-07 | 2015-02-06 | Conjugués et pro-drogues pour le traitement du cancer et de maladies inflammatoires |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017506628A JP2017506628A (ja) | 2017-03-09 |
| JP2017506628A5 true JP2017506628A5 (enExample) | 2018-03-15 |
| JP6721512B2 JP6721512B2 (ja) | 2020-07-15 |
Family
ID=50829100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016550736A Active JP6721512B2 (ja) | 2014-02-07 | 2015-02-06 | がん及び炎症性疾患の治療のための結合体及びプロドラッグ |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10293021B2 (enExample) |
| EP (2) | EP3139963B1 (enExample) |
| JP (1) | JP6721512B2 (enExample) |
| CN (2) | CN106573071A (enExample) |
| CA (1) | CA2938501C (enExample) |
| DK (1) | DK3139963T3 (enExample) |
| ES (1) | ES2843798T3 (enExample) |
| FR (1) | FR3017298B1 (enExample) |
| WO (1) | WO2015118497A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10722593B2 (en) | 2015-10-02 | 2020-07-28 | Sirenas Llc | Anti-cancer compounds and conjugates thereof |
| CN108779146B (zh) * | 2016-03-29 | 2022-03-18 | 东丽株式会社 | 肽衍生物及其用途 |
| US11666657B2 (en) | 2017-05-16 | 2023-06-06 | Universite De Strasbourg | Protein-drug conjugates and their use in the treatment of cancers |
| AU2018375787B2 (en) * | 2017-11-30 | 2023-02-23 | Ladrx Corporation | Albumin-binding prodrugs of auristatin E derivatives |
| CN120078904A (zh) * | 2018-04-03 | 2025-06-03 | 辛迪维亚公司 | 细胞毒性药物的结合物和所述结合物的前体药物形式 |
| JP7620569B2 (ja) * | 2019-05-06 | 2025-01-23 | セーキョー | がん治療のための新規治療用ベクター及びプロドラッグ |
| FR3126982B1 (fr) * | 2021-09-14 | 2023-09-15 | Centre Nat Rech Scient | Vecteurs ciblant la beta-d-n-acetylglucosaminidase |
| CN116077674B (zh) * | 2022-12-26 | 2025-03-25 | 北京大学 | 生物分子-聚氮氧化物偶联物及其制备方法与应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2802205C (en) | 2002-07-31 | 2016-01-19 | Seattle Genetics, Inc. | Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease |
| PT3248613T (pt) * | 2005-07-18 | 2022-03-16 | Seagen Inc | Conjugados de ligante de fármaco e beta-glucuronida |
| FR2960153B1 (fr) * | 2010-05-20 | 2012-08-17 | Centre Nat Rech Scient | Nouveaux bras autoreactifs et prodrogues les comprenant |
-
2014
- 2014-02-07 FR FR1450956A patent/FR3017298B1/fr not_active Expired - Fee Related
-
2015
- 2015-02-06 ES ES15709742T patent/ES2843798T3/es active Active
- 2015-02-06 US US15/117,069 patent/US10293021B2/en active Active
- 2015-02-06 CN CN201580018638.0A patent/CN106573071A/zh active Pending
- 2015-02-06 JP JP2016550736A patent/JP6721512B2/ja active Active
- 2015-02-06 DK DK15709742.9T patent/DK3139963T3/da active
- 2015-02-06 CN CN202210334259.4A patent/CN114917358A/zh active Pending
- 2015-02-06 WO PCT/IB2015/050914 patent/WO2015118497A1/fr not_active Ceased
- 2015-02-06 EP EP15709742.9A patent/EP3139963B1/fr active Active
- 2015-02-06 EP EP20192895.9A patent/EP3766510A1/fr active Pending
- 2015-02-06 CA CA2938501A patent/CA2938501C/fr active Active
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