ES2899114T3 - Análogos de purina y 3-deazapurina como inhibidores de colina cinasa - Google Patents
Análogos de purina y 3-deazapurina como inhibidores de colina cinasa Download PDFInfo
- Publication number
- ES2899114T3 ES2899114T3 ES17746421T ES17746421T ES2899114T3 ES 2899114 T3 ES2899114 T3 ES 2899114T3 ES 17746421 T ES17746421 T ES 17746421T ES 17746421 T ES17746421 T ES 17746421T ES 2899114 T3 ES2899114 T3 ES 2899114T3
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- Prior art keywords
- comp
- chloro
- cyclohexanecarboxamide
- purin
- amino
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- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title description 8
- 229940043355 kinase inhibitor Drugs 0.000 title description 5
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 5
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- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 74
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 59
- 125000003118 aryl group Chemical group 0.000 claims abstract description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 17
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical group 0.000 claims abstract description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 8
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims description 147
- 125000000217 alkyl group Chemical group 0.000 claims description 70
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 18
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- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
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- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 10
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
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- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 210000000481 breast Anatomy 0.000 claims description 4
- FVLVBVSILSHUAF-UHFFFAOYSA-N n-benzyl-3,5-dimethyl-n-propan-2-ylbenzamide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N(C(C)C)CC1=CC=CC=C1 FVLVBVSILSHUAF-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
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- YNTJKQDWYXUTLZ-UHFFFAOYSA-N 2-(3-chlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=CC(Cl)=C1 YNTJKQDWYXUTLZ-UHFFFAOYSA-N 0.000 claims description 2
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- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
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- SXRGKPQFEAUQFM-UHFFFAOYSA-N tert-butyl N-[4-[2-[4-[(4-methylpiperazin-1-yl)methyl]anilino]-2-oxoethyl]phenyl]carbamate Chemical compound CN1CCN(CC1)CC1=CC=C(C=C1)NC(CC1=CC=C(C=C1)NC(OC(C)(C)C)=O)=O SXRGKPQFEAUQFM-UHFFFAOYSA-N 0.000 description 1
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
- CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
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- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
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- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/18—Bridged systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16181105 | 2016-07-25 | ||
| PCT/EP2017/068255 WO2018019681A1 (en) | 2016-07-25 | 2017-07-19 | Purine and 3-deazapurine analogues as choline kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2899114T3 true ES2899114T3 (es) | 2022-03-10 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES17746421T Active ES2899114T3 (es) | 2016-07-25 | 2017-07-19 | Análogos de purina y 3-deazapurina como inhibidores de colina cinasa |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10683292B2 (enExample) |
| EP (1) | EP3487857B1 (enExample) |
| JP (1) | JP6920411B2 (enExample) |
| CN (1) | CN109790164B (enExample) |
| ES (1) | ES2899114T3 (enExample) |
| WO (1) | WO2018019681A1 (enExample) |
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| CN109310695B (zh) | 2016-04-21 | 2022-04-01 | 阿斯特罗赛特制药公司 | 治疗神经和心血管病况的化合物和方法 |
| CN110183442A (zh) * | 2019-06-06 | 2019-08-30 | 无锡合全药业有限公司 | 一种1 -(乙氧羰基)咪唑并[1, 5]吡啶-6-羧酸的合成方法 |
| US20240368164A1 (en) * | 2021-04-28 | 2024-11-07 | Astrocyle Pharmaceuticals, Inc. | Purine nucleosides, their intermediates, and methods of preparation thereof |
| JP7856405B2 (ja) | 2021-11-17 | 2026-05-11 | 信越化学工業株式会社 | 有機膜形成用組成物、パターン形成方法並びに有機膜形成用化合物及び重合体 |
| WO2023205366A1 (en) * | 2022-04-20 | 2023-10-26 | Carthronix, Inc. | Small molecule modulators of gp130 signaling pathways |
| WO2024044751A2 (en) * | 2022-08-26 | 2024-02-29 | Wake Forest University Health Sciences | Peroxiredoxin 3 inhibitors and methods of use for treating cancer |
| CN115403593B (zh) * | 2022-09-22 | 2024-02-02 | 河南师范大学 | 一种环加成合成手性嘌呤[3,2-c]并噁唑化合物的方法 |
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| JP2528107B2 (ja) * | 1985-03-15 | 1996-08-28 | サマ−トン，ジエ−ムス | ポリヌクレオチド測定試薬と方法 |
| DE10139730A1 (de) * | 2001-08-13 | 2003-02-27 | Nanogen Recognomics Gmbh | Verfahren zur Herstellung CNA |
| ES2385219T3 (es) * | 2003-09-12 | 2012-07-19 | Merck Serono Sa | Derivados de sulfonamida para el tratamiento de diabetes |
| ES2237332B1 (es) | 2004-01-14 | 2006-11-01 | Consejo Sup. Investig. Cientificas | Derivados de piridinio y quinolinio. |
| ES2277568B1 (es) | 2005-12-30 | 2008-04-01 | Consejo Superior De Investigaciones Cientificas | Derivados de triterpenoquinona y triterpenofenoles y su aplicacion para el tratamiento de tumores y enfermedades parasitarias. |
| WO2009116074A2 (en) * | 2008-02-13 | 2009-09-24 | Cadila Healthcare Limited | Substituted benzimidazoles as cannabinoid modulator |
| US9273028B2 (en) * | 2010-10-29 | 2016-03-01 | Biogen Ma Inc. | Heterocyclic tyrosine kinase inhibitors |
| AU2012274156A1 (en) * | 2011-06-20 | 2014-01-23 | Traslational Cancer Drugs Pharma, S.L. | Method for predicting the clinical response to chemotherapy in a subject with cancer |
| US20130281445A1 (en) | 2011-09-22 | 2013-10-24 | Simon Everitt | Compounds useful as inhibitors of choline kinase |
| KR20140064987A (ko) | 2011-09-22 | 2014-05-28 | 버텍스 파마슈티칼스 인코포레이티드 | 콜린 키나제의 억제제로서 유용한 화합물 |
| CN104507923B (zh) * | 2012-08-02 | 2018-02-09 | 内尔维阿诺医学科学有限公司 | 作为激酶抑制剂的取代的吡咯类活性剂 |
| WO2014165216A1 (en) * | 2013-03-12 | 2014-10-09 | The Trustees Of The University Of Pennsylvania | Diagnosing and treating cancer |
| WO2014151761A1 (en) * | 2013-03-15 | 2014-09-25 | Ariad Pharmaceuticals, Inc. | Novel choline kinase inhibitors |
| WO2015151006A1 (en) * | 2014-03-29 | 2015-10-08 | Lupin Limited | Substituted purine compounds as btk inhibitors |
| ES2482290B1 (es) | 2014-06-05 | 2015-05-19 | Universidad De Granada | Inhibidores polares simétricos de colina cinasa con actividad antitumoral |
| EP3912979B1 (en) * | 2015-06-03 | 2026-03-25 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| US11236093B2 (en) * | 2016-05-04 | 2022-02-01 | B.C.I. Pharma | Adenine derivatives as protein kinase inhibitors |
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- 2017-07-19 JP JP2019503678A patent/JP6920411B2/ja active Active
- 2017-07-19 US US16/319,951 patent/US10683292B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN109790164B (zh) | 2022-01-25 |
| JP2019522018A (ja) | 2019-08-08 |
| EP3487857A1 (en) | 2019-05-29 |
| JP6920411B2 (ja) | 2021-08-18 |
| EP3487857B1 (en) | 2021-09-01 |
| US20190225615A1 (en) | 2019-07-25 |
| CN109790164A (zh) | 2019-05-21 |
| WO2018019681A1 (en) | 2018-02-01 |
| US10683292B2 (en) | 2020-06-16 |
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