JP2006519815A5 - - Google Patents
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- Publication number
- JP2006519815A5 JP2006519815A5 JP2006504814A JP2006504814A JP2006519815A5 JP 2006519815 A5 JP2006519815 A5 JP 2006519815A5 JP 2006504814 A JP2006504814 A JP 2006504814A JP 2006504814 A JP2006504814 A JP 2006504814A JP 2006519815 A5 JP2006519815 A5 JP 2006519815A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- reaction
- carried out
- alkyl group
- formula
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 8
- 238000000034 method Methods 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- PIJCNSMLEHEOKI-UHFFFAOYSA-N ethyl 2-fluoro-3-oxo-3-pyrimidin-4-ylpropanoate Chemical compound CCOC(=O)C(F)C(=O)C1=CC=NC=N1 PIJCNSMLEHEOKI-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- -1 4-pyridinyl Chemical group 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- OFJCCPUVEJNLKP-UHFFFAOYSA-N ethyl 2-fluoro-3-oxo-3-pyridin-4-ylpropanoate Chemical compound CCOC(=O)C(F)C(=O)C1=CC=NC=C1 OFJCCPUVEJNLKP-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03290568A EP1454900A1 (en) | 2003-03-07 | 2003-03-07 | Process for the preparation of pyridinyl and pyrimidinyl mono-fluorinated beta keto-esters |
| EP03290568.9 | 2003-03-07 | ||
| PCT/EP2004/003052 WO2004078725A1 (en) | 2003-03-07 | 2004-03-05 | Process for the preparation of pyridinyl and pyrimidinyl mono-fluorinated beta keto esters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006519815A JP2006519815A (ja) | 2006-08-31 |
| JP2006519815A5 true JP2006519815A5 (https=) | 2007-03-29 |
| JP4805809B2 JP4805809B2 (ja) | 2011-11-02 |
Family
ID=32799102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006504814A Expired - Fee Related JP4805809B2 (ja) | 2003-03-07 | 2004-03-05 | ピリジニル及びピリミジニルモノフッ素化βケトエステルの製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7135569B2 (https=) |
| EP (2) | EP1454900A1 (https=) |
| JP (1) | JP4805809B2 (https=) |
| CN (1) | CN100398518C (https=) |
| AT (1) | ATE353877T1 (https=) |
| DE (1) | DE602004004767T2 (https=) |
| ES (1) | ES2281786T3 (https=) |
| RU (1) | RU2330844C2 (https=) |
| WO (1) | WO2004078725A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP1928437A2 (en) | 2005-08-26 | 2008-06-11 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU556140A1 (ru) * | 1975-01-06 | 1977-04-30 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвийской Сср | (1-Оксоинданил-2)-пиридины в качестве промежуточных продуктов дл синтеза биологически активных соединений с способ их получени |
| US6300511B1 (en) * | 1997-07-18 | 2001-10-09 | F2 Chemicals Limited | Catalyzed fluorination of carbonyl compounds |
| US6455728B1 (en) * | 1999-11-01 | 2002-09-24 | Air Products And Chemicals, Inc. | Direct fluorination process for preparing high purity 2-fluoro-1,3-dicarbonyl compounds using oxygen as a radical scavenger |
| EP1295885A1 (en) * | 2001-09-21 | 2003-03-26 | Sanofi-Synthelabo | Substituted 2-pyridinyl-6,7,8,9-tetrahydropyrimido(1,2-a)pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo(1,2-a)pyrimidin-5(1H)one derivatives |
| AU2002350487C1 (en) * | 2001-09-21 | 2008-10-02 | Mitsubishi Pharma Corporation | Substituted 2-pyridinyl-6,7,8,9- tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)one derivatives |
| EP1295884A1 (en) * | 2001-09-21 | 2003-03-26 | Sanofi-Synthelabo | 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-a]Pyrimidin-4-one and 7-Pyrimidinyl-2,3-Dihydroimidazo[1,2-a]Pyrimidin-5(1H)one derivatives |
-
2003
- 2003-03-07 EP EP03290568A patent/EP1454900A1/en not_active Withdrawn
-
2004
- 2004-03-05 DE DE602004004767T patent/DE602004004767T2/de not_active Expired - Lifetime
- 2004-03-05 AT AT04717645T patent/ATE353877T1/de not_active IP Right Cessation
- 2004-03-05 RU RU2005131007/04A patent/RU2330844C2/ru not_active IP Right Cessation
- 2004-03-05 WO PCT/EP2004/003052 patent/WO2004078725A1/en not_active Ceased
- 2004-03-05 ES ES04717645T patent/ES2281786T3/es not_active Expired - Lifetime
- 2004-03-05 CN CNB200480009687XA patent/CN100398518C/zh not_active Expired - Fee Related
- 2004-03-05 JP JP2006504814A patent/JP4805809B2/ja not_active Expired - Fee Related
- 2004-03-05 EP EP04717645A patent/EP1603876B1/en not_active Expired - Lifetime
-
2005
- 2005-09-07 US US11/221,023 patent/US7135569B2/en not_active Expired - Lifetime
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