AU778735B2 - Fused azepinone cyclin dependent kinase inhibitors - Google Patents
Fused azepinone cyclin dependent kinase inhibitors Download PDFInfo
- Publication number
- AU778735B2 AU778735B2 AU45714/99A AU4571499A AU778735B2 AU 778735 B2 AU778735 B2 AU 778735B2 AU 45714/99 A AU45714/99 A AU 45714/99A AU 4571499 A AU4571499 A AU 4571499A AU 778735 B2 AU778735 B2 AU 778735B2
- Authority
- AU
- Australia
- Prior art keywords
- dihydro
- indolo
- ring
- benzazepin
- hydrogen
- 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.)
- Ceased
Links
- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 title abstract description 11
- 239000002875 cyclin dependent kinase inhibitor Substances 0.000 title abstract description 6
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 91
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- 238000000034 method Methods 0.000 claims abstract description 55
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- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 46
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- 102000020233 phosphotransferase Human genes 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 description 1
- CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 229960005314 suramin Drugs 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 102000013498 tau Proteins Human genes 0.000 description 1
- 108010026424 tau Proteins Proteins 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003571 thiolactams Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000009452 underexpressoin Effects 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 210000004509 vascular smooth muscle cell Anatomy 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU15009/01A AU780528B2 (en) | 1999-06-16 | 2001-01-16 | Fused azepinone cyclin dependent kinase inhibitors |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8961998P | 1998-06-16 | 1998-06-16 | |
| US60/089619 | 1998-06-16 | ||
| PCT/US1999/013579 WO1999065910A1 (en) | 1998-06-16 | 1999-06-16 | Fused azepinone cyclin dependent kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU15009/01A Addition AU780528B2 (en) | 1999-06-16 | 2001-01-16 | Fused azepinone cyclin dependent kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4571499A AU4571499A (en) | 2000-01-05 |
| AU778735B2 true AU778735B2 (en) | 2004-12-16 |
Family
ID=22218651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU45714/99A Ceased AU778735B2 (en) | 1998-06-16 | 1999-06-16 | Fused azepinone cyclin dependent kinase inhibitors |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6610684B2 (https=) |
| EP (1) | EP1086105B1 (https=) |
| JP (1) | JP4555476B2 (https=) |
| AT (1) | ATE318818T1 (https=) |
| AU (1) | AU778735B2 (https=) |
| CA (1) | CA2335115C (https=) |
| DE (1) | DE69930120T2 (https=) |
| WO (1) | WO1999065910A1 (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2804959B1 (fr) * | 2000-02-15 | 2006-04-28 | Centre Nat Rech Scient | Utilisation de derives de paullones pour la fabrication de medicaments |
| JP4527404B2 (ja) | 2002-04-04 | 2010-08-18 | エンゾン，インコーポレーテッド | インドールのポリマー性アシル誘導体 |
| DE10260618B4 (de) * | 2002-12-23 | 2005-06-09 | Faustus Forschungs Cie. Translational Cancer Research Gmbh | Tumorhemmende annellierte Azepinonderivate |
| PL1748691T3 (pl) * | 2004-05-12 | 2011-04-29 | Bayer Cropscience Ag | Sposób regulacji wzrostu roślin |
| WO2006089874A1 (en) * | 2005-02-22 | 2006-08-31 | Gpc Biotech Ag | Benzo[2,3]azepino[4,5-b]indol-6-ones |
| EP1757607A1 (en) | 2005-08-24 | 2007-02-28 | Molisa GmbH | N5-substituted benzo¬2,3|azepino¬4,5-b|indol-6-ones for treating tropical diseases |
| FR2899107B1 (fr) * | 2006-03-30 | 2008-06-13 | Neurokin Entpr Unipersonnelle | Utilisation de la (s)-roscovitine pour la fabrication d'un medicament |
| WO2009010298A2 (en) * | 2007-07-18 | 2009-01-22 | Technische Universität Carolo-Wilhelmina Zu Braunschweig | Paullone derivatives and its use |
| US8716308B2 (en) | 2008-01-11 | 2014-05-06 | Albany Molecular Research, Inc. | (1-azinone)-substituted pyridoindoles |
| JP2012504646A (ja) * | 2008-10-01 | 2012-02-23 | ザ ユニバーシティ オブ ノース カロライナ アット チャペル ヒル | 選択的サイクリン依存性キナーゼ４／６阻害剤を用いた化学療法化合物に対する造血系の防護 |
| CN102231983A (zh) * | 2008-10-01 | 2011-11-02 | 北卡罗来纳大学查珀尔希尔分校 | 使用选择性细胞周期蛋白依赖性激酶4/6抑制剂对抗电离辐射的造血防护 |
| EP2414358A1 (en) * | 2009-03-31 | 2012-02-08 | ArQule, Inc. | Substituted tetrahydropyrazolo-pyrido-azepin compounds |
| EP3406260B1 (en) | 2009-05-13 | 2020-09-23 | The University of North Carolina at Chapel Hill | Cyclin dependent kinase inhibitors and methods of use |
| WO2011003012A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle mch-1 antagonists, methods of making, and use thereof |
| US8637501B2 (en) * | 2009-07-01 | 2014-01-28 | Albany Molecular Research, Inc. | Azinone-substituted azepino[b]indole and pyrido-pyrrolo-azepine MCH-1 antagonists, methods of making, and use thereof |
| US9073925B2 (en) * | 2009-07-01 | 2015-07-07 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| US8629158B2 (en) * | 2009-07-01 | 2014-01-14 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| KR20120060201A (ko) | 2009-07-08 | 2012-06-11 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 기능적으로 분화된 체세포의 연장된 자기재생을 유도하는 방법 |
| WO2011112635A1 (en) | 2010-03-08 | 2011-09-15 | Sloan-Kettering Institute For Cancer Research | Cdc7 kinase inhibitors and uses thereof |
| EP2640394A4 (en) | 2010-11-17 | 2015-02-25 | Univ North Carolina | PROTECTION OF KIDNEY TISSUE FROM ISCHEMIA BY THE INHIBITION OF PROLEVERATIVE KINASES CDK4 AND CDK6 |
| WO2012088038A2 (en) | 2010-12-21 | 2012-06-28 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline mch-1 antagonists, methods of making, and uses thereof |
| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
| HK1222766A1 (zh) | 2013-03-15 | 2017-07-14 | G1治疗公司 | 高效的抗赘生剂和抗增生剂 |
| DK2968290T3 (da) | 2013-03-15 | 2019-11-25 | G1 Therapeutics Inc | Transient beskyttelse af normale celler under kemoterapi |
| WO2015161285A1 (en) | 2014-04-17 | 2015-10-22 | G1 Therapeutics, Inc. | Tricyclic lactams for use in the protection of hematopoietic stem and progenitor cells against ionizing radiation |
| WO2016040858A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Combinations and dosing regimes to treat rb-positive tumors |
| WO2016040848A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Treatment of rb-negative tumors using topoisomerase inhibitors in combination with cyclin dependent kinase 4/6 inhibitors |
| EA201891170A1 (ru) | 2015-11-18 | 2018-11-30 | Джензим Корпорейшн | Биомаркер поликистозной болезни почек и варианты его применения |
| US10988479B1 (en) | 2020-06-15 | 2021-04-27 | G1 Therapeutics, Inc. | Morphic forms of trilaciclib and methods of manufacture thereof |
| WO2022104206A1 (en) * | 2020-11-13 | 2022-05-19 | Neuron23, Inc. | Kinase modulators and methods of use thereof |
| EP4277897A1 (en) * | 2021-01-12 | 2023-11-22 | Chengdu Anticancer Bioscience, Ltd. | Fused azepine compounds and their use in the treatment of cancer |
| US12258345B1 (en) | 2023-12-12 | 2025-03-25 | King Faisal University | Pyrrolo[3,2-c]isoquinoline-2,3-dione compounds as CK2 inhibitors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3642779A (en) * | 1969-10-22 | 1972-02-15 | Robins Co Inc A H | Indolo(1 2-d)(1 4)benzodiazepin-6-ones |
| US5866702A (en) * | 1996-08-02 | 1999-02-02 | Cv Therapeutics, Incorporation | Purine inhibitors of cyclin dependent kinase 2 |
| ATE239020T1 (de) * | 1996-10-09 | 2003-05-15 | Schering Corp | Tricyclische verbindungen als ras-fpt inhibitoren |
-
1999
- 1999-06-16 WO PCT/US1999/013579 patent/WO1999065910A1/en not_active Ceased
- 1999-06-16 AT AT99928715T patent/ATE318818T1/de not_active IP Right Cessation
- 1999-06-16 JP JP2000554735A patent/JP4555476B2/ja not_active Expired - Fee Related
- 1999-06-16 AU AU45714/99A patent/AU778735B2/en not_active Ceased
- 1999-06-16 CA CA002335115A patent/CA2335115C/en not_active Expired - Fee Related
- 1999-06-16 DE DE69930120T patent/DE69930120T2/de not_active Expired - Lifetime
- 1999-06-16 EP EP99928715A patent/EP1086105B1/en not_active Expired - Lifetime
-
2000
- 2000-12-14 US US09/739,534 patent/US6610684B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1086105A1 (en) | 2001-03-28 |
| CA2335115C (en) | 2009-01-27 |
| CA2335115A1 (en) | 1999-12-23 |
| DE69930120D1 (de) | 2006-04-27 |
| US20020042412A1 (en) | 2002-04-11 |
| AU4571499A (en) | 2000-01-05 |
| EP1086105B1 (en) | 2006-03-01 |
| ATE318818T1 (de) | 2006-03-15 |
| US6610684B2 (en) | 2003-08-26 |
| JP4555476B2 (ja) | 2010-09-29 |
| WO1999065910A9 (en) | 2000-03-16 |
| JP2002518395A (ja) | 2002-06-25 |
| DE69930120T2 (de) | 2006-11-02 |
| WO1999065910A1 (en) | 1999-12-23 |
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Legal Events
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| PC1 | Assignment before grant (sect. 113) |
Owner name: THE GOVERNMENT OF THE UNITED STATES OF AMERICA, RE Free format text: THE FORMER OWNER WAS: THE GOVERNMENT OF THE UNITED STATES OF AMERICA, REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES, CONRAD KUNICK, LAURENT MEIJER |