JP2017519740A5 - - Google Patents
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- Publication number
- JP2017519740A5 JP2017519740A5 JP2016569825A JP2016569825A JP2017519740A5 JP 2017519740 A5 JP2017519740 A5 JP 2017519740A5 JP 2016569825 A JP2016569825 A JP 2016569825A JP 2016569825 A JP2016569825 A JP 2016569825A JP 2017519740 A5 JP2017519740 A5 JP 2017519740A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- methoxy
- methylbutanamide
- amino
- pyrrolidin
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 66
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 33
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- -1 azidomethyl Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229960005190 phenylalanine Drugs 0.000 claims description 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- VTXPZVSCKQOHJD-BYPYZUCNSA-N (2s)-2-(dimethylamino)-3-hydroxypropanamide Chemical compound CN(C)[C@@H](CO)C(N)=O VTXPZVSCKQOHJD-BYPYZUCNSA-N 0.000 claims description 2
- QOOQIPIZQFXWTP-UHNVWZDZSA-N (2s,3r)-2-(dimethylamino)-3-hydroxybutanamide Chemical compound C[C@@H](O)[C@H](N(C)C)C(N)=O QOOQIPIZQFXWTP-UHNVWZDZSA-N 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 229960000310 isoleucine Drugs 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462004084P | 2014-05-28 | 2014-05-28 | |
| US62/004,084 | 2014-05-28 | ||
| PCT/US2015/032704 WO2015183978A1 (en) | 2014-05-28 | 2015-05-27 | Derivatives of dolaproine-dolaisoleuine peptides |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020081698A Division JP6995160B2 (ja) | 2014-05-28 | 2020-05-07 | ドラプロイン‐ドライソロイインペプチド誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017519740A JP2017519740A (ja) | 2017-07-20 |
| JP2017519740A5 true JP2017519740A5 (https=) | 2018-07-05 |
Family
ID=54699722
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016569825A Pending JP2017519740A (ja) | 2014-05-28 | 2015-05-27 | ドラプロイン‐ドライソロイインペプチド誘導体 |
| JP2020081698A Active JP6995160B2 (ja) | 2014-05-28 | 2020-05-07 | ドラプロイン‐ドライソロイインペプチド誘導体 |
| JP2021202579A Active JP7292366B2 (ja) | 2014-05-28 | 2021-12-14 | ドラプロイン‐ドライソロイインペプチド誘導体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020081698A Active JP6995160B2 (ja) | 2014-05-28 | 2020-05-07 | ドラプロイン‐ドライソロイインペプチド誘導体 |
| JP2021202579A Active JP7292366B2 (ja) | 2014-05-28 | 2021-12-14 | ドラプロイン‐ドライソロイインペプチド誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US20170190735A1 (https=) |
| EP (1) | EP3149024B9 (https=) |
| JP (3) | JP2017519740A (https=) |
| KR (1) | KR102413079B1 (https=) |
| CN (1) | CN107041139A (https=) |
| ES (1) | ES2883023T3 (https=) |
| RU (1) | RU2747989C2 (https=) |
| SG (1) | SG11201609739UA (https=) |
| WO (1) | WO2015183978A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3149024B9 (en) * | 2014-05-28 | 2021-10-27 | Agensys, Inc. | Cytotoxic dolaproine-dolaisoleuine peptide derivatives for the treatment of cancer |
| WO2017058808A1 (en) * | 2015-10-02 | 2017-04-06 | Sirenas Llc | Anti-cancer compounds and conjugates thereof |
| EP4321522A1 (en) * | 2022-08-12 | 2024-02-14 | Seagen Inc. | Cytotoxic compounds and conjugates thereof |
| AU2024267769A1 (en) * | 2023-05-06 | 2025-10-16 | Remegen Co., Ltd. | Preparation method for intermediate of auristatin derivative |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69232552T2 (de) * | 1991-08-09 | 2002-10-31 | Teikoku Hormone Mfg. Co., Ltd. | Tetrapeptide Derivat |
| US6569834B1 (en) | 1992-12-03 | 2003-05-27 | George R. Pettit | Elucidation and synthesis of antineoplastic tetrapeptide w-aminoalkyl-amides |
| US5635483A (en) | 1992-12-03 | 1997-06-03 | Arizona Board Of Regents Acting On Behalf Of Arizona State University | Tumor inhibiting tetrapeptide bearing modified phenethyl amides |
| US5780588A (en) | 1993-01-26 | 1998-07-14 | Arizona Board Of Regents | Elucidation and synthesis of selected pentapeptides |
| JPH06234790A (ja) * | 1993-02-09 | 1994-08-23 | Teikoku Hormone Mfg Co Ltd | 新規テトラペプチドアミド誘導体 |
| KR100332254B1 (ko) * | 1993-10-01 | 2002-09-27 | 데이꼬꾸 조끼 세이야꾸 가부시키가이샤 | 신규인펩티드유도체 |
| US5521284A (en) * | 1994-08-01 | 1996-05-28 | Arizona Board Of Regents Acting On Behalf Of Arizona State University | Human cancer inhibitory pentapeptide amides and esters |
| US5530097A (en) * | 1994-08-01 | 1996-06-25 | Arizona Board Of Regents Acting On Behalf Of Arizona State University | Human cancer inhibitory peptide amides |
| 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 |
| 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 |
| ATE459364T1 (de) | 2003-10-22 | 2010-03-15 | Univ Johns Hopkins | Verbesserte bakteriolyse-kombinationstherapie für die behandlung von tumoren |
| KR20070050918A (ko) * | 2004-07-02 | 2007-05-16 | 뉴텍 파마 피엘씨 | 암의 치료 |
| WO2006132670A2 (en) | 2004-11-12 | 2006-12-14 | Seattle Genetics, Inc. | Auristatins having an aminobenzoic acid unit at the n terminus |
| CN101242816B (zh) * | 2005-06-30 | 2012-10-31 | 维罗贝股份有限公司 | Hcv抑制剂 |
| US7608592B2 (en) | 2005-06-30 | 2009-10-27 | Virobay, Inc. | HCV inhibitors |
| 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 |
| CN106986926A (zh) | 2008-01-30 | 2017-07-28 | 皮里斯股份公司 | 具有对人c‑met受体酪氨酸激酶的亲和性的泪脂质运载蛋白的突变蛋白及其获得方法 |
| EP2265283B1 (en) * | 2008-03-18 | 2014-09-03 | Seattle Genetics, Inc. | Auristatin drug linker conjugates |
| EP2276509B1 (en) | 2008-04-11 | 2016-06-15 | Seattle Genetics, Inc. | Detection and tratment of pancreatic, ovarian and other cancers |
| KR102023496B1 (ko) | 2011-04-21 | 2019-09-20 | 시애틀 지네틱스, 인크. | 신규 결합제-약물 콘주게이트 (adc) 및 그의 용도 |
| RU2566693C2 (ru) * | 2011-07-08 | 2015-10-27 | Сименс Акциенгезелльшафт | Система слоев с двухслойным металлическим слоем |
| US20130190248A1 (en) * | 2011-07-26 | 2013-07-25 | Agensys, Inc. | Substituted peptide analogs |
| MY168297A (en) | 2011-11-17 | 2018-10-23 | Pfizer | Cytotoxic Peptides and Antibody Drug Conjugates Thereof |
| US9981046B2 (en) * | 2012-05-15 | 2018-05-29 | Concortis Biosystems, Corp., a wholly owned Subsidiary of Sorrento Therapeutics, Inc. | Drug-conjugates, conjugation methods, and uses thereof |
| HK1214282A1 (zh) * | 2012-11-07 | 2016-07-22 | 辉瑞公司 | 抗-notch3抗体及抗体-药物缀合物 |
| CN104936621A (zh) | 2012-11-07 | 2015-09-23 | 辉瑞公司 | 抗IL-13受体α2抗体和抗体-药物缀合物 |
| EP3149024B9 (en) * | 2014-05-28 | 2021-10-27 | Agensys, Inc. | Cytotoxic dolaproine-dolaisoleuine peptide derivatives for the treatment of cancer |
-
2015
- 2015-05-27 EP EP15799069.8A patent/EP3149024B9/en active Active
- 2015-05-27 ES ES15799069T patent/ES2883023T3/es active Active
- 2015-05-27 RU RU2016150426A patent/RU2747989C2/ru not_active Application Discontinuation
- 2015-05-27 US US15/313,906 patent/US20170190735A1/en not_active Abandoned
- 2015-05-27 KR KR1020167036764A patent/KR102413079B1/ko active Active
- 2015-05-27 CN CN201580041582.0A patent/CN107041139A/zh active Pending
- 2015-05-27 WO PCT/US2015/032704 patent/WO2015183978A1/en not_active Ceased
- 2015-05-27 JP JP2016569825A patent/JP2017519740A/ja active Pending
- 2015-05-27 SG SG11201609739UA patent/SG11201609739UA/en unknown
-
2019
- 2019-11-14 US US16/684,208 patent/US11312748B2/en active Active
-
2020
- 2020-05-07 JP JP2020081698A patent/JP6995160B2/ja active Active
-
2021
- 2021-12-14 JP JP2021202579A patent/JP7292366B2/ja active Active
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