ZA200506074B - Substitution derivatives of N6-benzyladenosine, methods of their preparation, their use for preperation of drugs, cosmetic preparations and growth regulators, pharmaceutical preparations, cosmetic preparations and growth regulators containing these compounds - Google Patents
Substitution derivatives of N6-benzyladenosine, methods of their preparation, their use for preperation of drugs, cosmetic preparations and growth regulators, pharmaceutical preparations, cosmetic preparations and growth regulators containing these compounds Download PDFInfo
- Publication number
- ZA200506074B ZA200506074B ZA200506074A ZA200506074A ZA200506074B ZA 200506074 B ZA200506074 B ZA 200506074B ZA 200506074 A ZA200506074 A ZA 200506074A ZA 200506074 A ZA200506074 A ZA 200506074A ZA 200506074 B ZA200506074 B ZA 200506074B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydroxy
- purine riboside
- chloro
- fluoro
- amino
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 72
- 238000002360 preparation method Methods 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 24
- 238000006467 substitution reaction Methods 0.000 title claims description 24
- 239000003814 drug Substances 0.000 title claims description 17
- 239000003630 growth substance Substances 0.000 title claims description 16
- 229940079593 drug Drugs 0.000 title claims description 14
- 239000002537 cosmetic Substances 0.000 title claims description 13
- MRPKNNSABYPGBF-LSCFUAHRSA-N (2r,3r,4s,5r)-2-[6-(benzylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical class O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(NCC=3C=CC=CC=3)=C2N=C1 MRPKNNSABYPGBF-LSCFUAHRSA-N 0.000 title claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- -1 amino, hydrazo Chemical group 0.000 claims description 936
- MRWXACSTFXYYMV-FDDDBJFASA-N nebularine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 claims description 643
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 112
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 108
- 210000004027 cell Anatomy 0.000 claims description 107
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 100
- 125000004432 carbon atom Chemical group C* 0.000 claims description 91
- 125000001153 fluoro group Chemical group F* 0.000 claims description 88
- 150000008223 ribosides Chemical class 0.000 claims description 88
- 125000001424 substituent group Chemical group 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
- 125000001246 bromo group Chemical group Br* 0.000 claims description 42
- 125000003368 amide group Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- 125000004423 acyloxy group Chemical group 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000003282 alkyl amino group Chemical group 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 36
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
- 125000004414 alkyl thio group Chemical group 0.000 claims description 35
- 125000004442 acylamino group Chemical group 0.000 claims description 34
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 34
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 31
- 125000000304 alkynyl group Chemical group 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000003367 polycyclic group Chemical group 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 230000009758 senescence Effects 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000004437 phosphorous atom Chemical group 0.000 claims description 7
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 210000002950 fibroblast Anatomy 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 230000035755 proliferation Effects 0.000 claims description 6
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 5
- 206010052779 Transplant rejections Diseases 0.000 claims description 5
- 238000004113 cell culture Methods 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 4
- IOPUAMVSOMUEDA-UHFFFAOYSA-N 2,5-dimethoxy-4-[(7h-purin-6-ylamino)methyl]phenol Chemical compound C1=C(O)C(OC)=CC(CNC=2C=3NC=NC=3N=CN=2)=C1OC IOPUAMVSOMUEDA-UHFFFAOYSA-N 0.000 claims description 4
- LFLSCGLVSMEKGW-UHFFFAOYSA-N 2-methoxy-4-[(7h-purin-6-ylamino)methyl]phenol Chemical compound C1=C(O)C(OC)=CC(CNC=2C=3NC=NC=3N=CN=2)=C1 LFLSCGLVSMEKGW-UHFFFAOYSA-N 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 4
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- DRFDMBPPWUNZFX-UHFFFAOYSA-N [2-[(7h-purin-6-ylamino)methyl]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1CNC1=NC=NC2=C1NC=N2 DRFDMBPPWUNZFX-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- HTFODAFEUYNHMV-UHFFFAOYSA-N n-[(2-chloro-4-fluorophenyl)methyl]-7h-purin-6-amine Chemical compound ClC1=CC(F)=CC=C1CNC1=NC=NC2=C1NC=N2 HTFODAFEUYNHMV-UHFFFAOYSA-N 0.000 claims description 4
- UIPBJXUABCBASK-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methyl]-7h-purin-6-amine Chemical compound C1=C(OC)C(OC)=CC=C1CNC1=NC=NC2=C1NC=N2 UIPBJXUABCBASK-UHFFFAOYSA-N 0.000 claims description 4
- UTZWZZICQOYTFM-UHFFFAOYSA-N n-[(3-chloro-2,6-difluorophenyl)methyl]-7h-purin-6-amine Chemical compound FC1=CC=C(Cl)C(F)=C1CNC1=NC=NC2=C1NC=N2 UTZWZZICQOYTFM-UHFFFAOYSA-N 0.000 claims description 4
- PGPCCTUFQQKBIZ-UHFFFAOYSA-N n-[(4-ethoxyphenyl)methyl]-7h-purin-6-amine Chemical compound C1=CC(OCC)=CC=C1CNC1=NC=NC2=C1NC=N2 PGPCCTUFQQKBIZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- QMXCKKNYBDZYHP-UHFFFAOYSA-N 1-[2-[(7h-purin-6-ylamino)methyl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1CNC1=NC=NC2=C1NC=N2 QMXCKKNYBDZYHP-UHFFFAOYSA-N 0.000 claims description 3
- KFYXVCOVDDKZIG-UHFFFAOYSA-N 2-[(7h-purin-6-ylamino)methyl]benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(CNC=2C=3NC=NC=3N=CN=2)=C1 KFYXVCOVDDKZIG-UHFFFAOYSA-N 0.000 claims description 3
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- LTRKHMLOGIPCHM-UHFFFAOYSA-N 2,3-dimethoxy-6-[(7H-purin-6-ylamino)methyl]phenol Chemical compound OC1=C(OC)C(OC)=CC=C1CNC1=NC=NC2=C1NC=N2 LTRKHMLOGIPCHM-UHFFFAOYSA-N 0.000 claims description 2
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- MXRKRIWYTXSKRU-UHFFFAOYSA-N 2-[(7h-purin-6-ylamino)methyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1CNC1=NC=NC2=C1NC=N2 MXRKRIWYTXSKRU-UHFFFAOYSA-N 0.000 claims description 2
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- YEDYIWLGLKTTFX-UHFFFAOYSA-N 2-chloro-6-[(7h-purin-6-ylamino)methyl]phenol Chemical compound OC1=C(Cl)C=CC=C1CNC1=NC=NC2=C1NC=N2 YEDYIWLGLKTTFX-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/606—Nucleosides; Nucleotides; Nucleic acids
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ20024273A CZ294538B6 (cs) | 2002-12-30 | 2002-12-30 | Substituční deriváty N6-benzyladenosinu, způsob jejich přípravy, jejich použití pro přípravu léčiv, kosmetických přípravků a růstových regulátorů, farmaceutické přípravky, kosmetické přípravky a růstové regulátory tyto sloučeniny obsahující |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200506074B true ZA200506074B (en) | 2006-05-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200506074A ZA200506074B (en) | 2002-12-30 | 2005-07-28 | Substitution derivatives of N6-benzyladenosine, methods of their preparation, their use for preperation of drugs, cosmetic preparations and growth regulators, pharmaceutical preparations, cosmetic preparations and growth regulators containing these compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8119614B2 (cs) |
| EP (1) | EP1575973B1 (cs) |
| AU (1) | AU2003294608A1 (cs) |
| CZ (1) | CZ294538B6 (cs) |
| WO (1) | WO2004058791A2 (cs) |
| ZA (1) | ZA200506074B (cs) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| PL1699459T3 (pl) * | 2003-12-29 | 2007-12-31 | Can Fite Biopharma Ltd | Sposób leczenia stwardnienia rozsianego |
| US20070183995A1 (en) * | 2006-02-09 | 2007-08-09 | Conopco, Inc., D/B/A Unilever | Compounds useful as agonists of A2A adenosine receptors, cosmetic compositions with A2A agonists and a method for using the same |
| US8129357B2 (en) * | 2006-04-07 | 2012-03-06 | Academia Sinica | Method of making and using an adenosine analogue |
| US7351434B2 (en) * | 2006-04-07 | 2008-04-01 | Academia Sinica | Therapeutic Gastrodia extracts |
| US7897737B2 (en) | 2006-12-05 | 2011-03-01 | Lasergen, Inc. | 3′-OH unblocked, nucleotides and nucleosides, base modified with photocleavable, terminating groups and methods for their use in DNA sequencing |
| MX338089B (es) * | 2006-12-05 | 2016-04-01 | Lasergen Inc | Nucleotidos y necleosidos marcados de foto-escision y necleotidos y necleosidos marcados y metodos para su uso en secuenciacion de adn. |
| US7893227B2 (en) | 2006-12-05 | 2011-02-22 | Lasergen, Inc. | 3′-OH unblocked nucleotides and nucleosides base modified with non-cleavable, terminating groups and methods for their use in DNA sequencing |
| EP2307565B1 (en) | 2008-06-11 | 2017-11-29 | Lasergen, Inc. | Reversible nucleosides and nucleotides terminators and their use in dna sequencing |
| JP2012503651A (ja) * | 2008-09-26 | 2012-02-09 | エージェンシー フォー サイエンス，テクノロジー アンド リサーチ | ３−デアザネプラノシン誘導体 |
| CZ2009298A3 (cs) * | 2009-05-14 | 2010-11-24 | Univerzita Palackého v Olomouci | Substituované 6-benzylaminopurin ribosidy, jejich použití a farmaceutický prípravek tyto slouceniny obsahující |
| TWI490219B (zh) | 2009-06-29 | 2015-07-01 | Incyte Corp | 作為ｐｉ３ｋ抑制劑之嘧啶酮 |
| CZ302618B6 (cs) | 2009-09-10 | 2011-08-03 | Univerzita Palackého | Cyklobutan-1,1-dikarboxylátokomplexy platiny s deriváty N6-benzyladeninu, zpusoby jejich prípravy a použití techto komplexu jako léciv v protinádorové terapii |
| CN106377540B (zh) * | 2009-11-13 | 2019-08-16 | 中央研究院 | 预防及治疗神经退化疾病的双功能化合物 |
| EP2511283A4 (en) * | 2009-12-10 | 2013-07-03 | Inst Materia Medica Cams | N6-SUBSTITUTED ADENOSINE DERIVATIVES, N6-SUBSTITUTED ADENINE DERIVATIVES AND THEIR USE |
| US8759359B2 (en) * | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| TW201130842A (en) * | 2009-12-18 | 2011-09-16 | Incyte Corp | Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors |
| JP5816678B2 (ja) | 2010-04-14 | 2015-11-18 | インサイト・コーポレイションＩｎｃｙｔｅ Ｃｏｒｐｏｒａｔｉｏｎ | ＰＩ３Ｋδ阻害剤としての縮合誘導体 |
| CZ303327B6 (cs) | 2010-04-29 | 2012-08-01 | Univerzita Palackého v Olomouci | Substitucní deriváty N6-benzyladenosin-5´-monofosfátu, zpusoby jejich prípravy, tyto deriváty pro použití jako léciva a terapeutický prípravek je obsahující |
| WO2011163195A1 (en) | 2010-06-21 | 2011-12-29 | Incyte Corporation | Fused pyrrole derivatives as pi3k inhibitors |
| TW201249844A (en) | 2010-12-20 | 2012-12-16 | Incyte Corp | N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors |
| JP6577165B2 (ja) * | 2011-01-26 | 2019-09-18 | 北京康倍得医▲藥▼技▲術▼▲開▼▲發▼有限公司 | リボフラノシルプリン化合物、その調製方法、およびその使用 |
| CN102617680B (zh) * | 2011-02-01 | 2014-04-02 | 复旦大学 | 一种双功能抗血小板聚集药物及其用途 |
| US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
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| CR20180293A (es) | 2011-09-02 | 2018-09-19 | Incyte Holdings Corp | HETEROCICLILAMINAS COMO INHIBIDORES DE PI3K (Divisional 2014-0111) |
| AU2012308518B2 (en) | 2011-09-13 | 2017-08-17 | Agilent Technologies, Inc. | 5-methoxy, 3'-oh unblocked, fast photocleavable terminating nucleotides and methods for nucleic acid sequencing |
| AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
| CZ306894B6 (cs) | 2013-02-08 | 2017-08-30 | Univerzita PalackĂ©ho v Olomouci | 2-Substituované-6-biarylmethylamino-9-cyklopentyl-9H-purinové deriváty, jejich použití jako léčiva a farmaceutické přípravky tyto sloučeniny obsahující |
| WO2014145386A2 (en) * | 2013-03-15 | 2014-09-18 | University Of Florida Research Foundation Incorporated | Novel allosteric inhibitors of thymidylate synthase |
| WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
| CZ308881B6 (cs) * | 2014-12-09 | 2021-08-04 | Univerzita Palackého v Olomouci | 6-aryl-9-glykosylpuriny a jejich použití |
| SG11201706917WA (en) | 2015-02-27 | 2017-09-28 | Incyte Corp | Salts of pi3k inhibitor and processes for their preparation |
| WO2016183060A1 (en) | 2015-05-11 | 2016-11-17 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| US9988401B2 (en) | 2015-05-11 | 2018-06-05 | Incyte Corporation | Crystalline forms of a PI3K inhibitor |
| US10835524B2 (en) | 2015-06-24 | 2020-11-17 | University Of Florida Research Foundation, Incorporated | Compositions for the treatment of pancreatic cancer and uses thereof |
| JP2015172077A (ja) * | 2015-06-24 | 2015-10-01 | 中国医学科学院葯物研究所 | Ｎ６−置換アデノシン誘導体とｎ６−置換アデニン誘導体の鎮静、催眠、抗うつ、抗痙攣、抗てんかん、抗パーキンソン病と認知証予防・治療の用途 |
| CN108329372B (zh) * | 2017-01-20 | 2022-07-26 | 浙江省亚热带作物研究所 | N6-(2-羟乙基)腺苷及其衍生物在制备治疗痛风药物中的应用 |
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| EP4178959B1 (en) | 2020-07-13 | 2025-09-10 | Univerzita Palackého v Olomouci | Nitrogen heterocyclic cytokinin derivatives, compositions containing these derivatives and use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3506643A (en) * | 1966-12-09 | 1970-04-14 | Max Thiel | N**6-aralkyl-adenosine derivatives |
| NL6717061A (cs) * | 1966-12-21 | 1968-06-24 | ||
| DE2007273A1 (de) * | 1970-02-18 | 1971-08-26 | Boehnnger Mannheim GmbH, 6800 Mann heim Waldhof | N(6) Aralkyl adenosin Derivate und Verfahren zur Herstellung derselben |
| DE2059922A1 (de) * | 1970-12-05 | 1972-06-15 | Boehringer Mannheim Gmbh | Neue N(6)-Aralkyl-adenosin-Derivate und Verfahren zur Herstellung derselben |
| DE2136624A1 (de) * | 1971-07-22 | 1973-02-08 | Boehringer Mannheim Gmbh | N (6)-substituierte adenosin-derivate und verfahren zur herstellung derselben |
| US4514405A (en) * | 1981-09-17 | 1985-04-30 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Use of adenosine derivatives as anticonvulsants |
| AU659861B2 (en) | 1991-09-10 | 1995-06-01 | Sansho Seiyaku Co., Ltd. | Preparation for promoting hair growth |
| EP0708781B1 (en) * | 1993-07-13 | 2001-10-04 | THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, Department of Health and Human Services | A 3 adenosine receptor agonists |
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2002
- 2002-12-30 CZ CZ20024273A patent/CZ294538B6/cs not_active IP Right Cessation
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2003
- 2003-12-29 US US10/540,993 patent/US8119614B2/en not_active Expired - Fee Related
- 2003-12-29 AU AU2003294608A patent/AU2003294608A1/en not_active Abandoned
- 2003-12-29 EP EP03785482.5A patent/EP1575973B1/en not_active Expired - Lifetime
- 2003-12-29 WO PCT/CZ2003/000078 patent/WO2004058791A2/en not_active Application Discontinuation
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| AU2003294608A8 (en) | 2004-07-22 |
| CZ20024273A3 (en) | 2004-08-18 |
| US20060166925A1 (en) | 2006-07-27 |
| CZ294538B6 (cs) | 2005-01-12 |
| EP1575973A2 (en) | 2005-09-21 |
| AU2003294608A1 (en) | 2004-07-22 |
| EP1575973B1 (en) | 2017-08-23 |
| WO2004058791A2 (en) | 2004-07-15 |
| US8119614B2 (en) | 2012-02-21 |
| WO2004058791A3 (en) | 2004-10-28 |
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