RU2747989C2 - Производные пептидов долапроин-долаизолейина - Google Patents
Производные пептидов долапроин-долаизолейина Download PDFInfo
- Publication number
- RU2747989C2 RU2747989C2 RU2016150426A RU2016150426A RU2747989C2 RU 2747989 C2 RU2747989 C2 RU 2747989C2 RU 2016150426 A RU2016150426 A RU 2016150426A RU 2016150426 A RU2016150426 A RU 2016150426A RU 2747989 C2 RU2747989 C2 RU 2747989C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- methoxy
- amino
- pyrrolidin
- methylbutanamido
- Prior art date
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- 108090000765 processed proteins & peptides Proteins 0.000 title abstract description 6
- 102000004196 processed proteins & peptides Human genes 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 224
- 238000000034 method Methods 0.000 claims abstract description 134
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 35
- 201000011510 cancer Diseases 0.000 claims abstract description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 6
- -1 —CONR b R c Chemical group 0.000 claims description 332
- 125000000217 alkyl group Chemical group 0.000 claims description 151
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 102
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 91
- 229910052799 carbon Inorganic materials 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 35
- 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 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 229960005190 phenylalanine Drugs 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
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- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0205—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/03—Peptides having up to 20 amino acids in an undefined or only partially defined sequence; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/07—Tetrapeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
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- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
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- Epidemiology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2016150426A RU2016150426A (ru) | 2018-07-03 |
| RU2016150426A3 RU2016150426A3 (https=) | 2018-12-20 |
| RU2747989C2 true RU2747989C2 (ru) | 2021-05-18 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2016150426A RU2747989C2 (ru) | 2014-05-28 | 2015-05-27 | Производные пептидов долапроин-долаизолейина |
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=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
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| EP0598129A1 (en) * | 1991-08-09 | 1994-05-25 | Teikoku Hormone Mfg. Co., Ltd. | Novel tetrapeptide derivative |
| EP0695758A2 (en) * | 1994-08-01 | 1996-02-07 | Arizona Board Of Regents | Human cancer inhibitory pentapeptide amides and esters |
| EP0695757A2 (en) * | 1994-08-01 | 1996-02-07 | Arizona Board Of Regents | Human cancer inhibitory peptide amides |
| WO2002088172A2 (en) * | 2001-04-30 | 2002-11-07 | Seattle Genetics, Inc. | Pentapeptide compounds and uses related thereto |
| WO2007008603A1 (en) * | 2005-07-07 | 2007-01-18 | Seattle Genetics, Inc. | Monomethylvaline compounds having phenylalanine side-chain modifications at the c-terminus |
| RU2010145942A (ru) * | 2008-04-11 | 2012-05-20 | Сиэтл Дженетикс, Инк. (Us) | Диагностика и лечение злокачественных опухолей поджелудочной железы, яичников и других злокачественных опухолей |
| WO2013173393A1 (en) * | 2012-05-15 | 2013-11-21 | Concortis Biosystems, Corp | Drug-conjugates, conjugation methods, and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0598129A1 (en) * | 1991-08-09 | 1994-05-25 | Teikoku Hormone Mfg. Co., Ltd. | Novel tetrapeptide derivative |
| EP0695758A2 (en) * | 1994-08-01 | 1996-02-07 | Arizona Board Of Regents | Human cancer inhibitory pentapeptide amides and esters |
| EP0695757A2 (en) * | 1994-08-01 | 1996-02-07 | Arizona Board Of Regents | Human cancer inhibitory peptide amides |
| WO2002088172A2 (en) * | 2001-04-30 | 2002-11-07 | Seattle Genetics, Inc. | Pentapeptide compounds and uses related thereto |
| WO2007008603A1 (en) * | 2005-07-07 | 2007-01-18 | Seattle Genetics, Inc. | Monomethylvaline compounds having phenylalanine side-chain modifications at the c-terminus |
| RU2010145942A (ru) * | 2008-04-11 | 2012-05-20 | Сиэтл Дженетикс, Инк. (Us) | Диагностика и лечение злокачественных опухолей поджелудочной железы, яичников и других злокачественных опухолей |
| WO2013173393A1 (en) * | 2012-05-15 | 2013-11-21 | Concortis Biosystems, Corp | Drug-conjugates, conjugation methods, and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017519740A (ja) | 2017-07-20 |
| KR102413079B1 (ko) | 2022-06-24 |
| WO2015183978A1 (en) | 2015-12-03 |
| EP3149024A1 (en) | 2017-04-05 |
| JP7292366B2 (ja) | 2023-06-16 |
| JP2022027896A (ja) | 2022-02-14 |
| US20220204557A1 (en) | 2022-06-30 |
| EP3149024B9 (en) | 2021-10-27 |
| US20200325170A1 (en) | 2020-10-15 |
| CN107041139A (zh) | 2017-08-11 |
| JP2020128405A (ja) | 2020-08-27 |
| RU2016150426A3 (https=) | 2018-12-20 |
| JP6995160B2 (ja) | 2022-01-14 |
| US20170190735A1 (en) | 2017-07-06 |
| US11312748B2 (en) | 2022-04-26 |
| KR20170005495A (ko) | 2017-01-13 |
| ES2883023T3 (es) | 2021-12-03 |
| RU2016150426A (ru) | 2018-07-03 |
| EP3149024A4 (en) | 2018-06-06 |
| EP3149024B1 (en) | 2021-05-12 |
| SG11201609739UA (en) | 2016-12-29 |
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