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 (3) | US20170190735A1 (https=) |
| EP (1) | EP3149024B9 (https=) |
| JP (3) | JP2017519740A (https=) |
| KR (1) | KR102413079B1 (https=) |
| CN (2) | CN121949442A (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 |
|---|---|---|---|---|
| WO2015183978A1 (en) * | 2014-05-28 | 2015-12-03 | Agensys, Inc. | Derivatives of dolaproine-dolaisoleuine peptides |
| 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 |
| CN120917016A (zh) * | 2023-05-06 | 2025-11-07 | 荣昌生物制药(烟台)股份有限公司 | 一种奥瑞他汀衍生物中间体的制备方法 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993003054A1 (fr) * | 1991-08-09 | 1993-02-18 | Teikoku Hormone Mfg. Co., Ltd. | Nouveau derive de tetrapeptide |
| 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 |
| US6569834B1 (en) | 1992-12-03 | 2003-05-27 | George R. Pettit | Elucidation and synthesis of antineoplastic tetrapeptide w-aminoalkyl-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 |
| EP0731106B1 (en) | 1993-10-01 | 2004-11-17 | Teikoku Hormone Mfg. Co., Ltd. | Dolastatin derivatives |
| US5530097A (en) * | 1994-08-01 | 1996-06-25 | Arizona Board Of Regents Acting On Behalf Of Arizona State University | Human cancer inhibitory peptide amides |
| 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 |
| 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 |
| US20030083263A1 (en) * | 2001-04-30 | 2003-05-01 | Svetlana Doronina | Pentapeptide compounds and uses related thereto |
| US7008928B2 (en) * | 2001-09-20 | 2006-03-07 | Teikoku Hormone Mfg. Co., Ltd. | Tetrapeptide derivative TZT-1027 crystal |
| EP1675465B1 (en) | 2003-10-22 | 2010-03-03 | The Johns Hopkins University | Improved combination bacteriolytic therapy for the treatment of tumors |
| CA2572318A1 (en) * | 2004-07-02 | 2006-01-12 | Neutec Pharma Plc | Treatment of cancer |
| US8288352B2 (en) * | 2004-11-12 | 2012-10-16 | Seattle Genetics, Inc. | Auristatins having an aminobenzoic acid unit at the N terminus |
| US7608592B2 (en) | 2005-06-30 | 2009-10-27 | Virobay, Inc. | HCV inhibitors |
| CN101242816B (zh) * | 2005-06-30 | 2012-10-31 | 维罗贝股份有限公司 | Hcv抑制剂 |
| ES2708763T3 (es) * | 2005-07-07 | 2019-04-11 | Seattle Genetics Inc | Compuestos de monometilvalina que tienen modificaciones de la cadena lateral de fenilalanina en el extremo C |
| CN101932598B (zh) | 2008-01-30 | 2016-12-21 | 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 |
| DK2265283T3 (da) * | 2008-03-18 | 2014-10-20 | Seattle Genetics Inc | Auristatin-lægemiddel-linker-konjugater |
| US9120854B2 (en) * | 2008-04-11 | 2015-09-01 | Seattle Genetics, Inc. | Detection and treatment of pancreatic, ovarian and other cancers |
| BR112013027119A8 (pt) | 2011-04-21 | 2018-03-06 | Seattle Genetics Inc | novos conjugados ligante-droga (adcs) e uso dos mesmos |
| 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 |
| CN104185477B (zh) * | 2011-11-17 | 2017-05-24 | 辉瑞公司 | 细胞毒性肽及其抗体‑药物缀合物 |
| CN104640572B (zh) * | 2012-05-15 | 2018-04-27 | 索伦托医疗有限公司 | 药物偶联物，偶联方法，及其用途 |
| KR101763499B1 (ko) * | 2012-11-07 | 2017-07-31 | 화이자 인코포레이티드 | 항-il-13 수용체 알파 2 항체 및 항체-약물 접합체 |
| CA2890571A1 (en) | 2012-11-07 | 2014-05-15 | Kenneth G. Geles | Anti-notch3 antibodies and antibody-drug conjugates |
| WO2015183978A1 (en) * | 2014-05-28 | 2015-12-03 | Agensys, Inc. | Derivatives of dolaproine-dolaisoleuine peptides |
-
2015
- 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 CN CN202610089819.2A patent/CN121949442A/zh active Pending
- 2015-05-27 SG SG11201609739UA patent/SG11201609739UA/en unknown
- 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 ES ES15799069T patent/ES2883023T3/es active Active
- 2015-05-27 CN CN201580041582.0A patent/CN107041139A/zh active Pending
- 2015-05-27 KR KR1020167036764A patent/KR102413079B1/ko active Active
- 2015-05-27 EP EP15799069.8A patent/EP3149024B9/en active Active
-
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
-
2022
- 2022-03-18 US US17/698,353 patent/US12612429B2/en active Active
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