KR20030032944A - 피리도[2,3-ｄ]피리미딘 및 피리미도[4,5-ｄ]피리미딘뉴클레오시드 - Google Patents
피리도[2,3-ｄ]피리미딘 및 피리미도[4,5-ｄ]피리미딘뉴클레오시드 Download PDFInfo
- Publication number
- KR20030032944A KR20030032944A KR1020027014601A KR20027014601A KR20030032944A KR 20030032944 A KR20030032944 A KR 20030032944A KR 1020027014601 A KR1020027014601 A KR 1020027014601A KR 20027014601 A KR20027014601 A KR 20027014601A KR 20030032944 A KR20030032944 A KR 20030032944A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- pyrimidine
- compound
- cells
- pyrido
- 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.)
- Abandoned
Links
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 title abstract description 29
- QGDYVSSVBYMOJN-UHFFFAOYSA-N pyrimido[4,5-d]pyrimidine Chemical compound C1=NC=NC2=NC=NC=C21 QGDYVSSVBYMOJN-UHFFFAOYSA-N 0.000 title abstract description 7
- 239000002718 pyrimidine nucleoside Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 229940002612 prodrug Drugs 0.000 claims abstract description 20
- 239000000651 prodrug Substances 0.000 claims abstract description 20
- 235000000346 sugar Nutrition 0.000 claims abstract description 14
- 210000004881 tumor cell Anatomy 0.000 claims abstract description 11
- 230000004614 tumor growth Effects 0.000 claims abstract description 5
- 210000004027 cell Anatomy 0.000 claims description 63
- 239000002777 nucleoside Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 24
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 21
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 229940127073 nucleoside analogue Drugs 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 230000006907 apoptotic process Effects 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000006366 phosphorylation reaction Methods 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
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- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 2
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- -1 and C 2 ′ Chemical compound 0.000 abstract description 16
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- RZYRVMWYQOETOI-UHFFFAOYSA-N 4-amino-6h-pyrido[2,3-d]pyrimidin-5-one Chemical compound N1=CCC(=O)C2=C1N=CN=C2N RZYRVMWYQOETOI-UHFFFAOYSA-N 0.000 description 14
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 230000004044 response Effects 0.000 description 11
- 201000011510 cancer Diseases 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- KWESCYLKRQKBTN-WOUKDFQISA-N 4-amino-8-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrido[2,3-d]pyrimidin-5-one Chemical compound C1=CC(=O)C=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O KWESCYLKRQKBTN-WOUKDFQISA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 5
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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
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21641800P | 2000-07-06 | 2000-07-06 | |
| US60/216,418 | 2000-07-06 |
Publications (1)
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|---|---|
| KR20030032944A true KR20030032944A (ko) | 2003-04-26 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020027014601A Abandoned KR20030032944A (ko) | 2000-07-06 | 2001-07-03 | 피리도[2,3-ｄ]피리미딘 및 피리미도[4,5-ｄ]피리미딘뉴클레오시드 |
Country Status (19)
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|---|---|
| US (1) | US7081449B2 (https=) |
| EP (1) | EP1303282A4 (https=) |
| JP (1) | JP2004522694A (https=) |
| KR (1) | KR20030032944A (https=) |
| CN (1) | CN1440292A (https=) |
| AU (2) | AU7367001A (https=) |
| BR (1) | BR0111531A (https=) |
| CA (1) | CA2405798A1 (https=) |
| CZ (1) | CZ20024052A3 (https=) |
| HU (1) | HUP0301614A3 (https=) |
| IL (1) | IL151849A0 (https=) |
| MX (1) | MXPA02012156A (https=) |
| NO (1) | NO20030033L (https=) |
| NZ (1) | NZ521457A (https=) |
| PL (1) | PL359559A1 (https=) |
| SK (1) | SK112003A3 (https=) |
| UA (1) | UA72612C2 (https=) |
| WO (1) | WO2002003997A1 (https=) |
| ZA (1) | ZA200208010B (https=) |
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| EP1964569A3 (en) | 2000-04-13 | 2009-07-22 | Pharmasset, Inc. | 3'-or 2'-hydroxymethyl substituted nucleoside derivatives for treatment of viral infections |
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| KR20080021797A (ko) | 2000-05-26 | 2008-03-07 | 이데닉스(케이만)리미티드 | 플라비바이러스 및 페스티바이러스의 치료방법 및 조성물 |
| AU2003231765B9 (en) | 2002-04-26 | 2010-01-28 | Gilead Sciences, Inc. | Cellular accumulation of phosphonate analogs of HIV protease inhibitor compounds and the compounds as such |
| NZ537662A (en) | 2002-06-28 | 2007-10-26 | Idenix Cayman Ltd | 2'-C-methyl-3'-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| PL374781A1 (en) | 2002-06-28 | 2005-10-31 | Idenix (Cayman) Limited | 2'-c-methyl-3'-o-l-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| JP2006507235A (ja) | 2002-08-01 | 2006-03-02 | フアーマセツト・インコーポレイテツド | フラビウイルス科ウイルス感染治療のためのビシクロ［４．２．１］ノナン系を有する化合物 |
| HUE033832T2 (en) | 2002-11-15 | 2018-01-29 | Idenix Pharmaceuticals Llc | 2'-methyl nucleosides in combination with interferon and Flaviviridae mutation |
| RU2005121904A (ru) | 2002-12-12 | 2006-01-20 | Айденикс (Кайман) Лимитед (Ky) | Способ получения 2`-разветвленных нуклеозидов |
| WO2004096287A2 (en) | 2003-04-25 | 2004-11-11 | Gilead Sciences, Inc. | Inosine monophosphate dehydrogenase inhibitory phosphonate compounds |
| MXPA05011296A (es) | 2003-04-25 | 2006-01-24 | Gilead Sciences Inc | Conjugados de fosfonato inhibidores de la cinasa. |
| US7452901B2 (en) | 2003-04-25 | 2008-11-18 | Gilead Sciences, Inc. | Anti-cancer phosphonate analogs |
| EP2359833A1 (en) | 2003-04-25 | 2011-08-24 | Gilead Sciences, Inc. | Antiviral phosphonate analogs |
| US7470724B2 (en) | 2003-04-25 | 2008-12-30 | Gilead Sciences, Inc. | Phosphonate compounds having immuno-modulatory activity |
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| US3423398A (en) | 1965-05-10 | 1969-01-21 | Pfizer & Co C | Sangivamycin and derivatives thereof |
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| HUP0301614A2 (hu) | 2003-09-29 |
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| CA2405798A1 (en) | 2002-01-17 |
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| PL359559A1 (en) | 2004-08-23 |
| BR0111531A (pt) | 2004-07-06 |
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| UA72612C2 (en) | 2005-03-15 |
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| EP1303282A1 (en) | 2003-04-23 |
| AU7367001A (en) | 2002-01-21 |
| CZ20024052A3 (cs) | 2003-03-12 |
| AU2001273670B2 (en) | 2005-07-14 |
| US7081449B2 (en) | 2006-07-25 |
| NO20030033L (no) | 2003-01-03 |
| JP2004522694A (ja) | 2004-07-29 |
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