SK280313B6 - N-(3-fluór-2-fosfonylmetoxypropyl)deriváty purínov - Google Patents
N-(3-fluór-2-fosfonylmetoxypropyl)deriváty purínov Download PDFInfo
- Publication number
- SK280313B6 SK280313B6 SK2047-90A SK204790A SK280313B6 SK 280313 B6 SK280313 B6 SK 280313B6 SK 204790 A SK204790 A SK 204790A SK 280313 B6 SK280313 B6 SK 280313B6
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- fluoro
- purine
- derivatives
- compound
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 10
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 17
- -1 pyrimidin-1-yl Chemical group 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012312 sodium hydride Substances 0.000 claims abstract description 9
- 229910000104 sodium hydride Inorganic materials 0.000 claims abstract description 9
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003212 purines Chemical class 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 241000700605 Viruses Species 0.000 claims abstract description 4
- 241001430294 unidentified retrovirus Species 0.000 claims abstract description 4
- LVOASXNJWPROPP-UHFFFAOYSA-N (4-methylphenyl)sulfonyloxymethylphosphonic acid Chemical compound CC1=CC=C(S(=O)(=O)OCP(O)(O)=O)C=C1 LVOASXNJWPROPP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 3
- 150000001721 carbon Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 51
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 20
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 claims description 10
- 238000001704 evaporation Methods 0.000 claims description 8
- 230000008020 evaporation Effects 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- OCAODLAHPGXQIE-UHFFFAOYSA-N 6-azido-7h-purin-2-amine Chemical group NC1=NC(N=[N+]=[N-])=C2NC=NC2=N1 OCAODLAHPGXQIE-UHFFFAOYSA-N 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 125000000848 adenin-9-yl group Chemical group [H]N([H])C1=C2N=C([H])N(*)C2=NC([H])=N1 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
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- 239000003814 drug Substances 0.000 claims description 2
- 125000003738 guanin-9-yl group Chemical group O=C1N([H])C(N([H])[H])=NC2=C1N=C([H])N2[*] 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004543 purin-7-yl group Chemical group N1=CN=C2N=CN(C2=C1)* 0.000 claims description 2
- BBSOSYZTRGLUKK-UHFFFAOYSA-N purine-2,6,6-triamine Chemical group NC1=NC(N)(N)C2=NC=NC2=N1 BBSOSYZTRGLUKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 abstract description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 12
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- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS902047A CZ285420B6 (cs) | 1990-04-24 | 1990-04-24 | N-(3-Fluor-2-fosfonylmethoxypropyl)deriváty purinových a pyrimidinových heterocyklických bazí, způsoby jejich přípravy a použití |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK280313B6 true SK280313B6 (sk) | 1999-11-08 |
Family
ID=5356430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK2047-90A SK280313B6 (sk) | 1990-04-24 | 1990-04-24 | N-(3-fluór-2-fosfonylmetoxypropyl)deriváty purínov |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5733896A (no) |
| EP (1) | EP0454427B1 (no) |
| JP (1) | JP2937532B2 (no) |
| AT (1) | ATE131171T1 (no) |
| AU (1) | AU7533091A (no) |
| CA (1) | CA2040982C (no) |
| CZ (1) | CZ285420B6 (no) |
| DE (1) | DE69115108T2 (no) |
| FI (1) | FI911980A (no) |
| IE (1) | IE911356A1 (no) |
| IL (1) | IL98110A0 (no) |
| NO (1) | NO911600L (no) |
| PT (1) | PT97478B (no) |
| SK (1) | SK280313B6 (no) |
| ZA (1) | ZA913033B (no) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ284678B6 (cs) * | 1991-05-20 | 1999-01-13 | Ústav Organické Chemie A Biochemie Avčr | Di(2-propyl)estery 1-fluor-2-fosfonomethoxy-3-p -toluensulfonyloxypropanů, způsob jejich přípravy a použití |
| US6057305A (en) * | 1992-08-05 | 2000-05-02 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Antiretroviral enantiomeric nucleotide analogs |
| US5977061A (en) * | 1995-04-21 | 1999-11-02 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | N6 - substituted nucleotide analagues and their use |
| US6093816A (en) | 1996-06-27 | 2000-07-25 | Isis Pharmaceuticals, Inc. | Cationic lipids |
| PT1045897E (pt) | 1998-01-23 | 2002-07-31 | Newbiotics Inc | Agentes terapeuticos por catalise enzimatica |
| US7462605B2 (en) * | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| EP1200130A2 (en) | 1999-07-22 | 2002-05-02 | Newbiotics, Inc. | Methods for treating therapy-resistant tumors |
| US6683061B1 (en) | 1999-07-22 | 2004-01-27 | Newbiotics, Inc. | Enzyme catalyzed therapeutic activation |
| AU2583901A (en) * | 1999-12-17 | 2001-06-25 | Ariad Pharmaceuticals, Inc. | Proton pump inhibitors |
| CN100402539C (zh) | 2000-07-21 | 2008-07-16 | 吉里德科学公司 | 核苷酸膦酸酯类似物前药及其筛选和制备方法 |
| US6747132B2 (en) | 2000-11-29 | 2004-06-08 | Apex Biosciences, Inc. | Methods for the synthesis of a modified hemoglobin solution |
| NZ530685A (en) | 2001-06-29 | 2006-09-29 | Acad Of Science Czech Republic | 6-'2-(phosphonomethoxy)alkoxy pyrimidine derivatives having antiviral activity |
| KR101102815B1 (ko) | 2003-06-16 | 2012-01-05 | 케이.유.루벤 리서치 앤드 디벨럽먼트 | 항바이러스 뉴클레오티드 유사체인 포스포네이트기를 갖는 피리미딘 화합물 |
| ES2401285T3 (es) * | 2004-12-16 | 2013-04-18 | The Regents Of The University Of California | Fármacos con el pulmón como diana |
| WO2006130217A2 (en) * | 2005-04-01 | 2006-12-07 | The Regents Of The University Of California | Substituted phosphate esters of nucleoside phosphonates |
| AU2006272521A1 (en) * | 2005-07-27 | 2007-02-01 | Gilead Sciences, Inc. | Antiviral phosphonate conjugates for inhibition of HIV |
| TWI444384B (zh) | 2008-02-20 | 2014-07-11 | Gilead Sciences Inc | 核苷酸類似物及其在治療惡性腫瘤上的用途 |
| MX2011004249A (es) * | 2008-10-24 | 2011-07-20 | Glaxosmithkline Biolog Sa | Derivados de imidazoquinolina lipidados. |
| ES2874774T3 (es) | 2011-12-22 | 2021-11-05 | Geron Corp | Análogos de guanina como sustratos de telomerasa y afectores de la longitud de los telómeros |
| PL2970346T3 (pl) | 2013-03-15 | 2019-02-28 | The Regents Of The University Of California | Acykliczne diestry fosfonianowe nukleozydów |
| PT3194411T (pt) | 2014-09-15 | 2022-06-06 | Univ California | Análogos de nucleótidos |
| EP3350191B9 (en) | 2015-09-15 | 2021-12-22 | The Regents of the University of California | Nucleotide analogs |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199574A (en) * | 1974-09-02 | 1980-04-22 | Burroughs Wellcome Co. | Methods and compositions for treating viral infections and guanine acyclic nucleosides |
| IL64501A (en) * | 1980-12-22 | 1985-07-31 | Astra Laekemedel Ab | 9-substituted 4-hydroxybutyl guanine derivatives,their preparation and antiviral use |
| US5047533A (en) * | 1983-05-24 | 1991-09-10 | Sri International | Acyclic purine phosphonate nucleotide analogs |
| CS264222B1 (en) * | 1986-07-18 | 1989-06-13 | Holy Antonin | N-phosphonylmethoxyalkylderivatives of bases of pytimidine and purine and method of use them |
| AU613592B2 (en) * | 1986-11-18 | 1991-08-08 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Antiviral phosophonomethoxy-alkyene purine and pyrimide derivatives |
| AU8092587A (en) * | 1986-11-18 | 1988-05-19 | Bristol-Myers Squibb Company | Synthesis of purin-9-ylalkylenoxymethyl phosphonic acids |
| US4808419A (en) * | 1987-02-02 | 1989-02-28 | Hsu Edward J | Automated method for a semi-solid fermentation used in the production of ancient quality rice vinegar and/or rice wine |
| ATE98249T1 (de) * | 1988-04-19 | 1993-12-15 | Merrell Dow Pharma | Phosphonoalkylpurin-derivate. |
| EP0338168A1 (en) * | 1988-04-19 | 1989-10-25 | Merrell Dow Pharmaceuticals Inc. | Phosphonoalkylpurine derivatives |
| JPH0296589A (ja) * | 1988-09-30 | 1990-04-09 | Asahi Glass Co Ltd | ヌクレオシド類 |
-
1990
- 1990-04-24 SK SK2047-90A patent/SK280313B6/sk not_active IP Right Cessation
- 1990-04-24 CZ CS902047A patent/CZ285420B6/cs not_active IP Right Cessation
-
1991
- 1991-04-23 ZA ZA913033A patent/ZA913033B/xx unknown
- 1991-04-23 AU AU75330/91A patent/AU7533091A/en not_active Abandoned
- 1991-04-23 NO NO91911600A patent/NO911600L/no unknown
- 1991-04-23 IE IE135691A patent/IE911356A1/en unknown
- 1991-04-23 CA CA002040982A patent/CA2040982C/en not_active Expired - Lifetime
- 1991-04-24 AT AT91303664T patent/ATE131171T1/de not_active IP Right Cessation
- 1991-04-24 FI FI911980A patent/FI911980A/fi not_active Application Discontinuation
- 1991-04-24 JP JP3094138A patent/JP2937532B2/ja not_active Expired - Lifetime
- 1991-04-24 PT PT97478A patent/PT97478B/pt not_active IP Right Cessation
- 1991-04-24 EP EP91303664A patent/EP0454427B1/en not_active Expired - Lifetime
- 1991-04-24 DE DE69115108T patent/DE69115108T2/de not_active Expired - Lifetime
- 1991-05-10 IL IL98110A patent/IL98110A0/xx unknown
-
1994
- 1994-03-18 US US08/210,255 patent/US5733896A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69115108T2 (de) | 1996-07-04 |
| JP2937532B2 (ja) | 1999-08-23 |
| CA2040982C (en) | 2001-12-04 |
| PT97478B (pt) | 1998-08-31 |
| DE69115108D1 (de) | 1996-01-18 |
| CA2040982A1 (en) | 1991-10-25 |
| NO911600D0 (no) | 1991-04-23 |
| FI911980A0 (fi) | 1991-04-24 |
| FI911980A (fi) | 1991-10-25 |
| IE911356A1 (en) | 1991-11-06 |
| JPH06206888A (ja) | 1994-07-26 |
| ATE131171T1 (de) | 1995-12-15 |
| NO911600L (no) | 1991-10-25 |
| AU7533091A (en) | 1991-11-07 |
| PT97478A (pt) | 1992-01-31 |
| CS9002047A2 (en) | 1991-11-12 |
| EP0454427A1 (en) | 1991-10-30 |
| EP0454427B1 (en) | 1995-12-06 |
| CZ285420B6 (cs) | 1999-08-11 |
| US5733896A (en) | 1998-03-31 |
| ZA913033B (en) | 1992-01-29 |
| IL98110A0 (en) | 1992-06-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20100424 |