ES2537451T3 - Procedimiento para preparar una 5H-pirimido[5,4-d][2]benzazepina - Google Patents
Procedimiento para preparar una 5H-pirimido[5,4-d][2]benzazepina Download PDFInfo
- Publication number
- ES2537451T3 ES2537451T3 ES12153134.7T ES12153134T ES2537451T3 ES 2537451 T3 ES2537451 T3 ES 2537451T3 ES 12153134 T ES12153134 T ES 12153134T ES 2537451 T3 ES2537451 T3 ES 2537451T3
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- ES
- Spain
- Prior art keywords
- compound
- formula
- cells
- cell
- pyrimido
- 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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- 238000000034 method Methods 0.000 title abstract description 5
- KZOWYKLEMRCPNH-UHFFFAOYSA-N 5h-pyrimido[5,4-d][2]benzazepine Chemical compound C1N=CC2=CC=CC=C2C2=NC=NC=C12 KZOWYKLEMRCPNH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 26
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 102000003989 Aurora kinases Human genes 0.000 description 8
- 108090000433 Aurora kinases Proteins 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000003556 assay Methods 0.000 description 5
- 239000003719 aurora kinase inhibitor Substances 0.000 description 5
- 229940123877 Aurora kinase inhibitor Drugs 0.000 description 4
- 230000004663 cell proliferation Effects 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- WOVKYSAHUYNSMH-RRKCRQDMSA-N 5-bromodeoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-RRKCRQDMSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 3
- 230000010261 cell growth Effects 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 230000035407 negative regulation of cell proliferation Effects 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000001516 cell proliferation assay Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000000099 in vitro assay Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 2-fluoro-6-methoxyphenyl Chemical group 0.000 description 1
- ZLHFILGSQDJULK-UHFFFAOYSA-N 4-[[9-chloro-7-(2-fluoro-6-methoxyphenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(NC=2N=C3C4=CC=C(Cl)C=C4C(=NCC3=CN=2)C=2C(=CC=CC=2F)OC)=C1 ZLHFILGSQDJULK-UHFFFAOYSA-N 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 231100000480 WST assay Toxicity 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000003782 apoptosis assay Methods 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 230000035578 autophosphorylation Effects 0.000 description 1
- 238000000423 cell based assay Methods 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 238000003570 cell viability assay Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000002900 effect on cell Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000005522 programmed cell death Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000163 radioactive labelling Methods 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Enzymes And Modification Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85934006P | 2006-11-16 | 2006-11-16 | |
| US859340P | 2006-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2537451T3 true ES2537451T3 (es) | 2015-06-08 |
Family
ID=39315133
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12153134.7T Active ES2537451T3 (es) | 2006-11-16 | 2007-11-14 | Procedimiento para preparar una 5H-pirimido[5,4-d][2]benzazepina |
| ES12153131.3T Active ES2528793T3 (es) | 2006-11-16 | 2007-11-14 | Compuestos para inhibir la progresión mitótica |
| ES07867449T Active ES2384123T3 (es) | 2006-11-16 | 2007-11-14 | Compuestos para inhibir la progresión mitótica |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12153131.3T Active ES2528793T3 (es) | 2006-11-16 | 2007-11-14 | Compuestos para inhibir la progresión mitótica |
| ES07867449T Active ES2384123T3 (es) | 2006-11-16 | 2007-11-14 | Compuestos para inhibir la progresión mitótica |
Country Status (34)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20080120T5 (hr) * | 2004-05-14 | 2012-07-31 | Millennium@Pharmaceuticals | Spojevi i postupci za inhibiciju napredovanja mitoze s pomoću inhibicije aurora kinaze |
| CL2007003244A1 (es) | 2006-11-16 | 2008-04-04 | Millennium Pharm Inc | Compuestos derivados de pirimido[5,4-d][2]benzazepina; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto para el tratamiento del cancer. |
| WO2010065134A1 (en) * | 2008-12-05 | 2010-06-10 | Millennium Pharmaceuticals, Inc. | 5, 7-dihydro- 6h-pyrimido [ 5, 4-d] [ 1 ] benzazepin-6-thiones as plk inhibitors |
| WO2010074724A1 (en) * | 2008-12-22 | 2010-07-01 | Millennium Pharmaceuticals, Inc. | Combination of aurora kinase inhibitors and anti-cd20 antibodies |
| JO3635B1 (ar) | 2009-05-18 | 2020-08-27 | Millennium Pharm Inc | مركبات صيدلانية صلبة وطرق لانتاجها |
| JO3434B1 (ar) * | 2009-07-31 | 2019-10-20 | Millennium Pharm Inc | مركبات صيدلانية لمعالجة السرطان وامراض واضطرابات اخري |
| RU2012140021A (ru) * | 2010-02-19 | 2014-03-27 | Миллениум Фармасьютикалз, Инк. | КРИСТАЛЛИЧЕСКИЕ ФОРМЫ 4-{[9-ХЛОР-7-(2-ФТОР-6-МЕТОКСИФЕНИЛ)-5Н-ПИРИМИДО[5,4-d][2]БЕНЗАЗЕПИН-2-ИЛ]АМИНО}-2-МЕТОКСИБЕНЗОАТА НАТРИЯ |
| US20120107304A1 (en) | 2010-04-27 | 2012-05-03 | Boehringer Ingelheim International Gmbh | Combination therapy in treatment of oncological and fibrotic diseases |
| JP5844358B2 (ja) * | 2010-06-22 | 2016-01-13 | グラクソスミスクライン エルエルシー | ベンゾトリアゾロジアゼピン化合物を含むブロモドメイン阻害剤 |
| UY34114A (es) | 2011-06-03 | 2013-01-03 | Millennium Pharm Inc | Combinación de inhibidores de mek e inhibidores selectivos de la quiinasa aurora a |
| US20130303519A1 (en) * | 2012-03-20 | 2013-11-14 | Millennium Pharmaceuticals, Inc. | Methods of treating cancer using aurora kinase inhibitors |
| CN103772391A (zh) * | 2012-10-23 | 2014-05-07 | 杨子娇 | 一类治疗房角狭窄的化合物及其用途 |
| EP2976086B1 (en) * | 2013-03-22 | 2020-10-14 | Millennium Pharmaceuticals, Inc. | Combination of catalytic mtorc 1/2 inhibitors and selective inhibitors of aurora a kinase |
| JP6525474B2 (ja) | 2013-12-06 | 2019-06-05 | ミレニアム ファーマシューティカルズ， インコーポレイテッドＭｉｌｌｅｎｎｉｕｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． | オーロラキナーゼ阻害剤と抗ｃｄ３０抗体の併用 |
| CA2972076A1 (en) * | 2014-12-23 | 2016-06-30 | Millennium Pharmaceuticals, Inc. | Combination of raf inhibitors and aurora kinase inhibitors |
| EP3324976A4 (en) | 2015-07-21 | 2019-03-27 | Millennium Pharmaceuticals, Inc. | ADMINISTRATION OF KINASE AURORA INHIBITOR AND CHEMOTHERAPEUTIC AGENTS |
| WO2017044567A1 (en) | 2015-09-09 | 2017-03-16 | Icahn School Of Medicine At Mount Sinai | Heterocyclic constrained tricyclic sulfonamides as anti-cancer agents |
| CA2997784A1 (en) | 2015-09-09 | 2017-03-16 | Icahn School Of Medicine At Mount Sinai | Heterocyclic constrained tricyclic sulfonamides as anti-cancer agents |
| WO2017146253A1 (ja) | 2016-02-26 | 2017-08-31 | 公益財団法人がん研究会 | Ｈｐ１の機能に着目した抗癌剤のスクリーニング方法及び評価系 |
| AU2017233898B2 (en) | 2016-03-15 | 2022-12-15 | Oryzon Genomics, S.A. | Combinations of LSD1 inhibitors for use in the treatment of solid tumors |
| JP6188986B1 (ja) * | 2017-03-23 | 2017-08-30 | 株式会社ノエビア | 時計遺伝子発現量調整剤及びエラスチン産生促進剤 |
| WO2019195658A1 (en) | 2018-04-05 | 2019-10-10 | Dana-Farber Cancer Institute, Inc. | Sting levels as a biomarker for cancer immunotherapy |
| WO2020049208A1 (es) | 2018-09-09 | 2020-03-12 | Fundacio Privada Institut De Recerca De La Sida - Caixa | Aurora cinasa como diana para tratar, prevenir o curar una infección por vih o sida |
| WO2021041532A1 (en) | 2019-08-26 | 2021-03-04 | Dana-Farber Cancer Institute, Inc. | Use of heparin to promote type 1 interferon signaling |
| WO2023196959A1 (en) | 2022-04-07 | 2023-10-12 | Eli Lilly And Company | Process for making a kras g12c inhibitor |
| CA3247183A1 (en) | 2022-04-08 | 2023-10-12 | Lilly Co Eli | TREATMENT METHOD INCLUDING KRAS G12C INHIBITORS AND AURORA A INHIBITORS |
| KR20250027777A (ko) | 2022-06-30 | 2025-02-27 | 일라이 릴리 앤드 캄파니 | 암을 치료하기 위한 kras g12c 억제제 |
| WO2025075211A1 (en) | 2023-10-03 | 2025-04-10 | Takeda Pharmaceutical Company Limited | Alisertib and paclitaxel for treating small cell lung cancer |
| WO2025245045A1 (en) | 2024-05-21 | 2025-11-27 | The Regents Of The University Of California | Methods of treating lung cancer |
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| HRP20080120T5 (hr) | 2004-05-14 | 2012-07-31 | Millennium@Pharmaceuticals | Spojevi i postupci za inhibiciju napredovanja mitoze s pomoću inhibicije aurora kinaze |
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| KR20080083680A (ko) | 2005-12-23 | 2008-09-18 | 스미스클라인 비참 코포레이션 | 오로라 키나제의 아자인돌 억제제 |
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| JO3635B1 (ar) * | 2009-05-18 | 2020-08-27 | Millennium Pharm Inc | مركبات صيدلانية صلبة وطرق لانتاجها |
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2007
- 2007-11-09 CL CL200703244A patent/CL2007003244A1/es unknown
- 2007-11-14 GE GEAP200711309A patent/GEP20125459B/en unknown
- 2007-11-14 MY MYPI20091846A patent/MY153243A/en unknown
- 2007-11-14 SG SG2011080652A patent/SG176443A1/en unknown
- 2007-11-14 PL PL07867449T patent/PL2086981T3/pl unknown
- 2007-11-14 PT PT07867449T patent/PT2086981E/pt unknown
- 2007-11-14 JP JP2009537199A patent/JP5102839B2/ja active Active
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- 2007-11-14 EP EP12153131.3A patent/EP2497772B1/en active Active
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- 2007-11-14 DK DK07867449.6T patent/DK2086981T3/da active
- 2007-11-14 SG SG10201503350TA patent/SG10201503350TA/en unknown
- 2007-11-14 UA UAA200906211A patent/UA94129C2/ru unknown
- 2007-11-14 NZ NZ611898A patent/NZ611898A/en not_active IP Right Cessation
- 2007-11-14 BR BRPI0718803A patent/BRPI0718803B8/pt active IP Right Grant
- 2007-11-14 EP EP07867449A patent/EP2086981B1/en active Active
- 2007-11-14 CN CN201310367332.9A patent/CN103483343B/zh active Active
- 2007-11-14 KR KR1020117022355A patent/KR101342014B1/ko active Active
- 2007-11-14 US US11/985,277 patent/US8026246B2/en active Active
- 2007-11-14 CN CN2007800423837A patent/CN101547924B/zh active Active
- 2007-11-14 AT AT07867449T patent/ATE556076T1/de active
- 2007-11-14 SI SI200730975T patent/SI2086981T1/sl unknown
- 2007-11-14 EA EA200970486A patent/EA015779B1/ru unknown
- 2007-11-14 KR KR1020097012501A patent/KR101110458B1/ko active Active
- 2007-11-14 ES ES12153134.7T patent/ES2537451T3/es active Active
- 2007-11-14 DK DK12153131.3T patent/DK2497772T3/en active
- 2007-11-14 HR HRP20120490TT patent/HRP20120490T1/hr unknown
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- 2007-11-14 ES ES12153131.3T patent/ES2528793T3/es active Active
- 2007-11-14 RS RS20150047A patent/RS53788B1/sr unknown
- 2007-11-14 ES ES07867449T patent/ES2384123T3/es active Active
- 2007-11-14 WO PCT/US2007/023948 patent/WO2008063525A1/en not_active Ceased
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