JP2014515735A5 - - Google Patents
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- Publication number
- JP2014515735A5 JP2014515735A5 JP2013558400A JP2013558400A JP2014515735A5 JP 2014515735 A5 JP2014515735 A5 JP 2014515735A5 JP 2013558400 A JP2013558400 A JP 2013558400A JP 2013558400 A JP2013558400 A JP 2013558400A JP 2014515735 A5 JP2014515735 A5 JP 2014515735A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- group
- optionally
- phenyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 25
- 206010028980 Neoplasm Diseases 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 230000002265 prevention Effects 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- -1 propene-1,3-diyl Chemical group 0.000 claims description 6
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 4
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000004504 1,2,4-oxadiazolyl group Chemical class 0.000 claims description 2
- 125000001781 1,3,4-oxadiazolyl group Chemical class 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002883 imidazolyl group Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical class 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 230000001028 anti-proliverative effect Effects 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 102000004169 proteins and genes Human genes 0.000 claims 4
- 108090000623 proteins and genes Proteins 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11158481 | 2011-03-16 | ||
| EP11158481.9 | 2011-03-16 | ||
| PCT/EP2012/054294 WO2012123423A1 (de) | 2011-03-16 | 2012-03-12 | N-carboxyalkyl-auristatine und ihre verwendung |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016145282A Division JP2016185987A (ja) | 2011-03-16 | 2016-07-25 | Ｎカルボキシアルキルオーリスタチンおよびその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014515735A JP2014515735A (ja) | 2014-07-03 |
| JP2014515735A5 true JP2014515735A5 (enExample) | 2015-07-02 |
| JP6023097B2 JP6023097B2 (ja) | 2016-11-09 |
Family
ID=45812791
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013558400A Active JP6023097B2 (ja) | 2011-03-16 | 2012-03-12 | Ｎカルボキシアルキルオーリスタチンおよびその使用 |
| JP2016145282A Withdrawn JP2016185987A (ja) | 2011-03-16 | 2016-07-25 | Ｎカルボキシアルキルオーリスタチンおよびその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016145282A Withdrawn JP2016185987A (ja) | 2011-03-16 | 2016-07-25 | Ｎカルボキシアルキルオーリスタチンおよびその使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9029406B2 (enExample) |
| EP (1) | EP2686336B1 (enExample) |
| JP (2) | JP6023097B2 (enExample) |
| CN (1) | CN103764667B (enExample) |
| CA (1) | CA2829736C (enExample) |
| ES (1) | ES2543888T3 (enExample) |
| WO (1) | WO2012123423A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2553874T3 (es) | 2010-09-29 | 2015-12-14 | Seattle Genetics, Inc. | N-Carboxialquil-auristatinas y su uso |
| EP3501546A3 (de) * | 2011-04-21 | 2019-09-18 | Seattle Genetics, Inc. | Cystein-wirkstoff konjugate und ihre verwendung |
| TWI589592B (zh) | 2011-11-17 | 2017-07-01 | 輝瑞股份有限公司 | 胞毒性肽類以及其抗體藥物共軛體 |
| WO2014093379A1 (en) | 2012-12-10 | 2014-06-19 | Mersana Therapeutics, Inc. | Auristatin compounds and conjugates thereof |
| FR3005051A1 (fr) * | 2013-04-25 | 2014-10-31 | Pf Medicament | Derives de la dolastatine 10 et d'auristatines |
| US10208125B2 (en) | 2013-07-15 | 2019-02-19 | University of Pittsburgh—of the Commonwealth System of Higher Education | Anti-mucin 1 binding agents and uses thereof |
| JP6636925B2 (ja) | 2013-12-17 | 2020-01-29 | ノバルティス アーゲー | 細胞障害性ペプチドおよびその抱合体 |
| ES2916722T3 (es) | 2013-12-27 | 2022-07-05 | Zymeworks Inc | Sistemas de enlace que contienen sulfonamida para conjugados de fármacos |
| CN106470708B (zh) | 2014-04-25 | 2019-12-31 | 皮埃尔法布雷医药公司 | 抗体-药物-缀合物和其用于治疗癌症的用途 |
| EP3134124B1 (en) | 2014-04-25 | 2019-02-20 | Pierre Fabre Medicament | Igf-1r antibody-drug-conjugate and its use for the treatment of cancer |
| EA201692530A1 (ru) | 2014-06-13 | 2017-07-31 | Новартис Аг | Цитотоксические пептиды и их конъюгаты |
| JP7350313B2 (ja) | 2016-12-16 | 2023-09-26 | ブルーフィン バイオメディシン， インコーポレイテッド | 抗ｃｕｂドメイン含有タンパク質１（ｃｄｃｐ１）抗体、抗体薬物コンジュゲート、およびその使用方法 |
| CN111393346B (zh) * | 2020-06-02 | 2020-08-25 | 凯莱英生命科学技术(天津)有限公司 | N-Boc-Dolaproine及Boc-Dap DCHA的合成方法 |
| EP4400121A1 (en) | 2021-09-03 | 2024-07-17 | Toray Industries, Inc. | Pharmaceutical composition for treating and/or preventing cancer |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5663149A (en) | 1994-12-13 | 1997-09-02 | Arizona Board Of Regents Acting On Behalf Of Arizona State University | Human cancer inhibitory pentapeptide heterocyclic and halophenyl amides |
| CA2315230C (en) | 1998-01-09 | 2004-06-29 | Arizona Board Of Regents, A Body Corporate, Acting On Behalf Of Arizona State University | Anti-cryptococcal peptides |
| MXPA01011502A (es) | 1999-05-14 | 2003-08-20 | Boehringer Ingelheim Pharma | Compuestos de tipo profarmaco anti-tumorigenos, activados por enzimas. |
| US6323315B1 (en) | 1999-09-10 | 2001-11-27 | Basf Aktiengesellschaft | Dolastatin peptides |
| US6884869B2 (en) | 2001-04-30 | 2005-04-26 | Seattle Genetics, Inc. | Pentapeptide compounds and uses related thereto |
| US6737409B2 (en) | 2001-07-19 | 2004-05-18 | Hoffmann-La Roche Inc. | Dolastatin 10 derivatives |
| WO2003026577A2 (en) | 2001-09-24 | 2003-04-03 | Seattle Genetics, Inc. | P-amidobenzylethers in drug delivery agents |
| ES2544527T3 (es) | 2002-07-31 | 2015-09-01 | Seattle Genetics, Inc. | Conjugados de fármacos y su uso para tratar el cáncer, una enfermedad autoinmune o una enfermedad infecciosa |
| EP3434275A1 (en) * | 2003-11-06 | 2019-01-30 | Seattle Genetics, Inc. | Assay for cancer cells based on the use of auristatin conjugates with antibodies |
| JP2008519863A (ja) | 2004-11-12 | 2008-06-12 | シアトル ジェネティクス インコーポレイティッド | Ｎ末端にアミノ安息香酸単位を有するオーリスタチン |
| WO2007008848A2 (en) | 2005-07-07 | 2007-01-18 | Seattle Genetics, Inc. | Monomethylvaline compounds having phenylalanine carboxy modifications at the c-terminus |
| JP5171621B2 (ja) | 2005-07-07 | 2013-03-27 | シアトル ジェネティックス， インコーポレイテッド | フェニルアラニン側鎖修飾をｃ末端に有するモノメチルバリン化合物 |
| AU2007308792B2 (en) | 2006-10-27 | 2013-01-24 | Genentech, Inc. | Antibodies and immunoconjugates and uses therefor |
| EP2265283B1 (en) | 2008-03-18 | 2014-09-03 | Seattle Genetics, Inc. | Auristatin drug linker conjugates |
| CA2801971C (en) * | 2010-06-10 | 2018-07-24 | Hans-Georg Lerchen | Novel auristatin derivatives and their use |
| ES2553874T3 (es) | 2010-09-29 | 2015-12-14 | Seattle Genetics, Inc. | N-Carboxialquil-auristatinas y su uso |
| EP3501546A3 (de) | 2011-04-21 | 2019-09-18 | Seattle Genetics, Inc. | Cystein-wirkstoff konjugate und ihre verwendung |
-
2012
- 2012-03-12 CA CA2829736A patent/CA2829736C/en active Active
- 2012-03-12 EP EP12708034.9A patent/EP2686336B1/de not_active Not-in-force
- 2012-03-12 US US14/004,699 patent/US9029406B2/en active Active
- 2012-03-12 WO PCT/EP2012/054294 patent/WO2012123423A1/de not_active Ceased
- 2012-03-12 CN CN201280019732.4A patent/CN103764667B/zh not_active Expired - Fee Related
- 2012-03-12 JP JP2013558400A patent/JP6023097B2/ja active Active
- 2012-03-12 ES ES12708034.9T patent/ES2543888T3/es active Active
-
2016
- 2016-07-25 JP JP2016145282A patent/JP2016185987A/ja not_active Withdrawn