DE602004004767T2 - Verfahren zur herstellung von monoifluorierten pyridinyl- und pyrimidinyl-beta-ketoestern - Google Patents
Verfahren zur herstellung von monoifluorierten pyridinyl- und pyrimidinyl-beta-ketoestern Download PDFInfo
- Publication number
- DE602004004767T2 DE602004004767T2 DE602004004767T DE602004004767T DE602004004767T2 DE 602004004767 T2 DE602004004767 T2 DE 602004004767T2 DE 602004004767 T DE602004004767 T DE 602004004767T DE 602004004767 T DE602004004767 T DE 602004004767T DE 602004004767 T2 DE602004004767 T2 DE 602004004767T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- alkyl group
- oxo
- pyridinyl
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 17
- -1 PYRIMIDINYL Chemical class 0.000 title claims description 9
- FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical class [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 239000011737 fluorine Substances 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 7
- 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 description 7
- 239000007789 gas Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 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 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 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 description 2
- PCJNYGPKMQQCPX-UHFFFAOYSA-N ethyl 3-oxo-3-pyridin-4-ylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=NC=C1 PCJNYGPKMQQCPX-UHFFFAOYSA-N 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XWOBORAWDRPNGZ-UHFFFAOYSA-N 2-fluoro-3-oxo-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(F)C(=O)C1=CC=NC=N1 XWOBORAWDRPNGZ-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C(*)(CF)C(OO*)=O)=O Chemical compound CC(C(*)(CF)C(OO*)=O)=O 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 description 1
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- IGRUUQSUGJLZCM-UHFFFAOYSA-N ethyl 3-oxo-3-pyrimidin-4-ylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=NC=N1 IGRUUQSUGJLZCM-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([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
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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 | 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 (2)
| Publication Number | Publication Date |
|---|---|
| DE602004004767D1 DE602004004767D1 (de) | 2007-03-29 |
| DE602004004767T2 true DE602004004767T2 (de) | 2007-12-06 |
Family
ID=32799102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602004004767T Expired - Lifetime DE602004004767T2 (de) | 2003-03-07 | 2004-03-05 | Verfahren zur herstellung von monoifluorierten pyridinyl- und pyrimidinyl-beta-ketoestern |
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
Also Published As
| Publication number | Publication date |
|---|---|
| ES2281786T3 (es) | 2007-10-01 |
| JP2006519815A (ja) | 2006-08-31 |
| EP1454900A1 (en) | 2004-09-08 |
| DE602004004767D1 (de) | 2007-03-29 |
| US7135569B2 (en) | 2006-11-14 |
| EP1603876A1 (en) | 2005-12-14 |
| RU2005131007A (ru) | 2006-06-27 |
| CN1771229A (zh) | 2006-05-10 |
| EP1603876B1 (en) | 2007-02-14 |
| RU2330844C2 (ru) | 2008-08-10 |
| ATE353877T1 (de) | 2007-03-15 |
| CN100398518C (zh) | 2008-07-02 |
| JP4805809B2 (ja) | 2011-11-02 |
| US20060058526A1 (en) | 2006-03-16 |
| WO2004078725A1 (en) | 2004-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |