NZ540722A - Process for the preparation of pyrimidine compounds and intermediates thereof - Google Patents
Process for the preparation of pyrimidine compounds and intermediates thereofInfo
- Publication number
- NZ540722A NZ540722A NZ540722A NZ54072203A NZ540722A NZ 540722 A NZ540722 A NZ 540722A NZ 540722 A NZ540722 A NZ 540722A NZ 54072203 A NZ54072203 A NZ 54072203A NZ 540722 A NZ540722 A NZ 540722A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- compound
- group
- alkyl
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 239000000543 intermediate Substances 0.000 title abstract description 4
- 150000003230 pyrimidines Chemical class 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 47
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 23
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- -1 pyrimidine compound Chemical class 0.000 claims abstract description 10
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 7
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical group O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 11
- 239000007800 oxidant agent Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000011369 resultant mixture Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 3
- 229960000789 guanidine hydrochloride Drugs 0.000 description 3
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- HNNFDXWDCFCVDM-UHFFFAOYSA-N methyl 4-methyl-3-oxopentanoate Chemical compound COC(=O)CC(=O)C(C)C HNNFDXWDCFCVDM-UHFFFAOYSA-N 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 229940001593 sodium carbonate Drugs 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229910003827 NRaRb Inorganic materials 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RMYXELUYVYVDAI-UHFFFAOYSA-N methyl 2-amino-4-(4-fluorophenyl)-6-propan-2-ylpyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(C(C)C)N=C(N)N=C1C1=CC=C(F)C=C1 RMYXELUYVYVDAI-UHFFFAOYSA-N 0.000 description 2
- UWAQJFHCXKILSF-UHFFFAOYSA-N methyl 2-amino-6-(4-fluorophenyl)-4-propan-2-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound N1=C(N)NC(C(C)C)C(C(=O)OC)=C1C1=CC=C(F)C=C1 UWAQJFHCXKILSF-UHFFFAOYSA-N 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052705 radium Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- XQYAEIDOJUNIGY-UHFFFAOYSA-N (2-iodo-5-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(I)C(B(O)O)=C1 XQYAEIDOJUNIGY-UHFFFAOYSA-N 0.000 description 1
- 150000005006 2-aminopyrimidines Chemical class 0.000 description 1
- VIQUKKCAYSMRHC-UHFFFAOYSA-N 4-(4-fluorophenyl)-6-propan-2-ylpyrimidin-2-amine Chemical compound NC1=NC(C(C)C)=CC(C=2C=CC(F)=CC=2)=N1 VIQUKKCAYSMRHC-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- LKOMIQVTMTVECF-UHFFFAOYSA-N 4-propan-2-ylpyrimidine-5-carboxylic acid Chemical compound CC(C)C1=NC=NC=C1C(O)=O LKOMIQVTMTVECF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WZKOEZKDTKPHOD-UHFFFAOYSA-N CC(C(CC(=O)OC)=O)C.CC(C(CC(=O)OC(C)C)=O)C Chemical compound CC(C(CC(=O)OC)=O)C.CC(C(CC(=O)OC(C)C)=O)C WZKOEZKDTKPHOD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- OBRYTFVFWHISJN-UHFFFAOYSA-N Cl.NC(=N)N.NC=1NC(C(=C(N1)C1=CC=C(C=C1)F)C(=O)OC(C)C)C(C)C Chemical compound Cl.NC(=N)N.NC=1NC(C(=C(N1)C1=CC=C(C=C1)F)C(=O)OC(C)C)C(C)C OBRYTFVFWHISJN-UHFFFAOYSA-N 0.000 description 1
- YNMOEUSBZLGDHC-UHFFFAOYSA-N Cl.NC(=N)N.NC=1NC(C(=C(N1)C1=CC=C(C=C1)F)C(=O)OCC)C(C)C Chemical compound Cl.NC(=N)N.NC=1NC(C(=C(N1)C1=CC=C(C=C1)F)C(=O)OCC)C(C)C YNMOEUSBZLGDHC-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- ZZCNKSMCIZCVDR-UHFFFAOYSA-N barium(2+);dioxido(dioxo)manganese Chemical compound [Ba+2].[O-][Mn]([O-])(=O)=O ZZCNKSMCIZCVDR-UHFFFAOYSA-N 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- QLXLISAWVGPSSW-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)-6-propan-2-ylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(C)C)N=C(N)N=C1C1=CC=C(F)C=C1 QLXLISAWVGPSSW-UHFFFAOYSA-N 0.000 description 1
- UGYAOPGIMIOTOE-UHFFFAOYSA-N ethyl 2-amino-6-(4-fluorophenyl)-4-propan-2-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound N1=C(N)NC(C(C)C)C(C(=O)OCC)=C1C1=CC=C(F)C=C1 UGYAOPGIMIOTOE-UHFFFAOYSA-N 0.000 description 1
- HXBVXMWOHMYUKM-UHFFFAOYSA-N ethyl 2-amino-6-(4-fluorophenyl)-4-propan-2-yl-1,4-dihydropyrimidine-5-carboxylate ethyl 2-amino-4-(4-fluorophenyl)-6-propan-2-ylpyrimidine-5-carboxylate Chemical compound NC=1NC(C(=C(N1)C1=CC=C(C=C1)F)C(=O)OCC)C(C)C.NC1=NC(=C(C(=N1)C1=CC=C(C=C1)F)C(=O)OCC)C(C)C HXBVXMWOHMYUKM-UHFFFAOYSA-N 0.000 description 1
- QWDLWJHZPSTJKL-UHFFFAOYSA-N ethyl 4-(4-fluorophenyl)-2-(methylamino)-6-propan-2-ylpyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=C(C(C)C)N=C(NC)N=C1C1=CC=C(F)C=C1 QWDLWJHZPSTJKL-UHFFFAOYSA-N 0.000 description 1
- JTXOTDJQFWHXEA-UHFFFAOYSA-N ethyl 6-(4-fluorophenyl)-2-(methylamino)-4-propan-2-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound N1=C(NC)NC(C(C)C)C(C(=O)OCC)=C1C1=CC=C(F)C=C1 JTXOTDJQFWHXEA-UHFFFAOYSA-N 0.000 description 1
- QJKIIKVRMCMCEO-UHFFFAOYSA-N ethyl 6-(4-fluorophenyl)-2-(methylamino)-4-propan-2-yl-1,4-dihydropyrimidine-5-carboxylate;2-methylguanidine;hydrochloride Chemical compound Cl.CN=C(N)N.N1C(NC)=NC(C(C)C)C(C(=O)OCC)=C1C1=CC=C(F)C=C1 QJKIIKVRMCMCEO-UHFFFAOYSA-N 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229960004198 guanidine Drugs 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- ZMDDIBOTLBHGNY-UHFFFAOYSA-N methyl 6-(4-fluorophenyl)-4-propan-2-yl-2-pyrazol-1-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound N1C(C(C)C)C(C(=O)OC)=C(C=2C=CC(F)=CC=2)N=C1N1C=CC=N1 ZMDDIBOTLBHGNY-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical group P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- LYTQYZZPBCKFTK-UHFFFAOYSA-N propan-2-yl 2-amino-6-(4-fluorophenyl)-4-propan-2-yl-1,4-dihydropyrimidine-5-carboxylate Chemical compound N1=C(N)NC(C(C)C)C(C(=O)OC(C)C)=C1C1=CC=C(F)C=C1 LYTQYZZPBCKFTK-UHFFFAOYSA-N 0.000 description 1
- RSNLWQKJOHYEAJ-UHFFFAOYSA-N propan-2-yl 4-methyl-3-oxopentanoate Chemical compound CC(C)OC(=O)CC(=O)C(C)C RSNLWQKJOHYEAJ-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- 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
- C07D239/28—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0229243A GB0229243D0 (en) | 2002-12-16 | 2002-12-16 | Compounds and process |
| GB0303589A GB0303589D0 (en) | 2003-02-17 | 2003-02-17 | Compounds and process |
| GB0318515A GB0318515D0 (en) | 2003-08-07 | 2003-08-07 | Compounds and process |
| PCT/GB2003/005359 WO2004054986A2 (en) | 2002-12-16 | 2003-12-09 | Process for the preparation of pyrimidine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ540722A true NZ540722A (en) | 2008-03-28 |
Family
ID=32600665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ540722A NZ540722A (en) | 2002-12-16 | 2003-12-09 | Process for the preparation of pyrimidine compounds and intermediates thereof |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US7524955B2 (enExample) |
| EP (2) | EP1578731B1 (enExample) |
| JP (2) | JP4579821B2 (enExample) |
| KR (1) | KR101060215B1 (enExample) |
| AR (1) | AR042355A1 (enExample) |
| AT (1) | ATE448209T1 (enExample) |
| AU (1) | AU2003288443B2 (enExample) |
| BR (1) | BR0317313A (enExample) |
| CA (1) | CA2509344C (enExample) |
| CY (1) | CY1110605T1 (enExample) |
| DE (1) | DE60330050D1 (enExample) |
| DK (1) | DK1578731T3 (enExample) |
| ES (1) | ES2335279T3 (enExample) |
| IL (1) | IL168884A (enExample) |
| MX (1) | MXPA05006425A (enExample) |
| MY (1) | MY138051A (enExample) |
| NO (2) | NO330983B1 (enExample) |
| NZ (1) | NZ540722A (enExample) |
| PT (1) | PT1578731E (enExample) |
| SI (1) | SI1578731T1 (enExample) |
| TW (1) | TWI322145B (enExample) |
| WO (1) | WO2004054986A2 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0011120D0 (en) | 2000-05-09 | 2000-06-28 | Avecia Ltd | Process |
| NL1015744C2 (nl) | 2000-07-19 | 2002-01-22 | Dsm Nv | Werkwijze voor de bereiding van 2-(6-gesubstitueerde-1,3-dioxan-4-yl) azijnzuurderivaten. |
| KR100888408B1 (ko) | 2001-07-13 | 2009-03-13 | 아스트라제네카 유케이 리미티드 | 아미노피리미딘 화합물의 제조 방법 |
| EP1323717A1 (en) | 2001-12-27 | 2003-07-02 | Dsm N.V. | Process for the preparation of 2-(6-Substituted-1,3-Dioxane-4-yL) acetic acid derivatives |
| KR20030092446A (ko) * | 2002-05-29 | 2003-12-06 | 주식회사 한국토종약초연구소 | 씨형 간염 활성 억제를 갖는 조릿대 추출물을 포함하는조성물 |
| EP1375493A1 (en) | 2002-06-17 | 2004-01-02 | Dsm N.V. | Process for the preparation of an dioxane acetic acid ester |
| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| DE60330050D1 (de) | 2002-12-16 | 2009-12-24 | Astrazeneca Uk Ltd | Verfahren zur herstellung von pyrimidinverbindungen |
| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| UY28501A1 (es) | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
| GB0324791D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| GB0428328D0 (en) * | 2004-12-24 | 2005-02-02 | Astrazeneca Uk Ltd | Chemical process |
| GB0514078D0 (en) * | 2005-07-08 | 2005-08-17 | Astrazeneca Uk Ltd | Chemical process |
| US8153791B2 (en) * | 2005-12-21 | 2012-04-10 | Janssen Pharmaceutica N.V. | Substituted pyrimidinyl oxime kinase inhibitors |
| WO2007109783A2 (en) * | 2006-03-23 | 2007-09-27 | Janssen Pharmaceutica, N.V. | Substituted pyrimidine kinase inhibitors |
| TW200831469A (en) * | 2006-12-01 | 2008-08-01 | Astrazeneca Uk Ltd | Chemical process |
| MX2012013475A (es) | 2010-05-21 | 2012-12-10 | Cooper Technologies Co | Adapatador para retenedor de buje. |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3278001A (en) * | 1965-02-02 | 1966-10-11 | Charles C Andrews | Bearing assembly for auger conveyors |
| US4698340A (en) | 1984-07-19 | 1987-10-06 | Fujisawa Pharmaceutical Co., Ltd. | Pyrimidine derivatives, processes for preparation thereof and composition containing the same |
| US4689414A (en) * | 1986-02-24 | 1987-08-25 | E. R. Squibb & Sons, Inc. | 2-(substituted imino)-6-aryl-3,6-dihydro-4-substituted-1,5(2H)-pyrimidinecarboxylic acids and analogs |
| WO1990003973A1 (en) * | 1988-10-06 | 1990-04-19 | Sandoz Ag | Pyrimidinyl-substituted hydroxyacids, lactones and esters and pharmaceutical compositions containing them |
| FR2665159B1 (fr) | 1990-07-24 | 1992-11-13 | Rhone Poulenc Sante | Nouveaux derives de la pyridine et de la quinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| JP2648897B2 (ja) | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | ピリミジン誘導体 |
| WO1993008823A1 (en) | 1991-11-06 | 1993-05-13 | Tanabe Seiyaku Co., Ltd. | Guanidinyl and related cell adhesion modulation compounds |
| JP3197971B2 (ja) * | 1993-03-01 | 2001-08-13 | 塩野義製薬株式会社 | ５−カルボアルコキシピリミジン誘導体の合成方法 |
| US5593992A (en) * | 1993-07-16 | 1997-01-14 | Smithkline Beecham Corporation | Compounds |
| NZ264063A (en) | 1993-08-13 | 1995-11-27 | Nihon Nohyaku Co Ltd | N-(2-phenylpyrid-3-yl)- and n-(4-phenylpyrimidin-5-yl)-n'-phenylurea derivatives and pharmaceutical compositions |
| CA2205384C (en) | 1994-11-16 | 2004-06-29 | Synaptic Pharmaceutical Corporation | Dihydropyrimidines and uses thereof |
| DE19517186A1 (de) * | 1995-05-11 | 1996-11-14 | Bayer Ag | Verfahren zur Herstellung substituierter 2-Fluor-pyrimidine |
| US6278001B1 (en) | 1995-11-28 | 2001-08-21 | L'oréal | Method for preparing (+) compactin and (+) mevinolin analog compounds having a β-hydroxy-δ-lactone grouping |
| FR2741620B1 (fr) | 1995-11-28 | 1997-12-26 | Oreal | Procede de preparation de composes a groupement beta-hydroxy -delta-lactone analogues de la (+) compactine et de la (+) mevinoline |
| NZ326039A (en) | 1995-12-14 | 1999-08-30 | Merck & Co Inc | Process for making 3,4-dihydro-pyrimidin-2(1h)-one derivatives |
| US5958934A (en) | 1996-05-23 | 1999-09-28 | Syntex (U.S.A.) Inc. | Aryl pyrimidine derivatives and uses thereof |
| SE9702563D0 (sv) | 1997-07-02 | 1997-07-02 | Astra Ab | Compounds |
| EP1003734A2 (en) | 1997-08-05 | 2000-05-31 | Merck & Co., Inc. | ALPHA 1a ADRENERGIC RECEPTOR ANTAGONIST |
| GB9903472D0 (en) * | 1999-02-17 | 1999-04-07 | Zeneca Ltd | Chemical process |
| WO2000078730A1 (en) | 1999-06-23 | 2000-12-28 | Ajinomoto Co., Inc. | Novel dihydropyrimidine derivatives |
| CZ304307B6 (cs) | 1999-07-13 | 2014-02-26 | Lonza Ag | Způsob výroby 2-amino-4-(4-fluorfenyl)-6-alkyl-pyrimidin-5-karboxylátu |
| GB0003305D0 (en) | 2000-02-15 | 2000-04-05 | Zeneca Ltd | Pyrimidine derivatives |
| AU2000254249A1 (en) | 2000-03-28 | 2001-10-08 | Biocon India Limited | Synthesis of (r-(r*,r*))-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1- |
| GB0011120D0 (en) | 2000-05-09 | 2000-06-28 | Avecia Ltd | Process |
| GB0011163D0 (en) | 2000-05-10 | 2000-06-28 | Astrazeneca Ab | Chemical compound |
| NL1015744C2 (nl) | 2000-07-19 | 2002-01-22 | Dsm Nv | Werkwijze voor de bereiding van 2-(6-gesubstitueerde-1,3-dioxan-4-yl) azijnzuurderivaten. |
| KR100888408B1 (ko) * | 2001-07-13 | 2009-03-13 | 아스트라제네카 유케이 리미티드 | 아미노피리미딘 화합물의 제조 방법 |
| EP1323717A1 (en) | 2001-12-27 | 2003-07-02 | Dsm N.V. | Process for the preparation of 2-(6-Substituted-1,3-Dioxane-4-yL) acetic acid derivatives |
| KR100511533B1 (ko) | 2002-04-09 | 2005-08-31 | 임광민 | 키랄 중간체, 그의 제조방법 및 그를 이용한 HMG-CoA환원저해제의 제조방법 |
| EP1375493A1 (en) | 2002-06-17 | 2004-01-02 | Dsm N.V. | Process for the preparation of an dioxane acetic acid ester |
| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| DE60330050D1 (de) | 2002-12-16 | 2009-12-24 | Astrazeneca Uk Ltd | Verfahren zur herstellung von pyrimidinverbindungen |
| WO2004103977A2 (en) | 2003-05-21 | 2004-12-02 | Ciba Specialty Chemicals Holding Inc. | Process for the preparation of pyrimidine derivatives |
| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| UY28501A1 (es) | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
| GB0321827D0 (en) | 2003-09-18 | 2003-10-15 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0324791D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| CA2645396A1 (en) | 2003-12-24 | 2005-07-14 | Teva Pharmaceutical Industries, Ltd | Process for preparation of statins with high syn to anti ratio |
| GB0428328D0 (en) | 2004-12-24 | 2005-02-02 | Astrazeneca Uk Ltd | Chemical process |
-
2003
- 2003-12-09 DE DE60330050T patent/DE60330050D1/de not_active Expired - Lifetime
- 2003-12-09 SI SI200331722T patent/SI1578731T1/sl unknown
- 2003-12-09 DK DK03780362.4T patent/DK1578731T3/da active
- 2003-12-09 US US10/537,723 patent/US7524955B2/en not_active Expired - Fee Related
- 2003-12-09 ES ES03780362T patent/ES2335279T3/es not_active Expired - Lifetime
- 2003-12-09 NZ NZ540722A patent/NZ540722A/en not_active IP Right Cessation
- 2003-12-09 JP JP2005502458A patent/JP4579821B2/ja not_active Expired - Fee Related
- 2003-12-09 MX MXPA05006425A patent/MXPA05006425A/es active IP Right Grant
- 2003-12-09 PT PT03780362T patent/PT1578731E/pt unknown
- 2003-12-09 AU AU2003288443A patent/AU2003288443B2/en not_active Ceased
- 2003-12-09 EP EP03780362A patent/EP1578731B1/en not_active Expired - Lifetime
- 2003-12-09 CA CA2509344A patent/CA2509344C/en not_active Expired - Fee Related
- 2003-12-09 AT AT03780362T patent/ATE448209T1/de active
- 2003-12-09 BR BR0317313-5A patent/BR0317313A/pt not_active IP Right Cessation
- 2003-12-09 EP EP09159247A patent/EP2088142A3/en not_active Ceased
- 2003-12-09 KR KR1020057010964A patent/KR101060215B1/ko not_active Expired - Fee Related
- 2003-12-09 WO PCT/GB2003/005359 patent/WO2004054986A2/en not_active Ceased
- 2003-12-10 AR ARP030104541A patent/AR042355A1/es unknown
- 2003-12-12 MY MYPI20034768A patent/MY138051A/en unknown
- 2003-12-16 TW TW092135557A patent/TWI322145B/zh not_active IP Right Cessation
-
2005
- 2005-05-30 IL IL168884A patent/IL168884A/en not_active IP Right Cessation
- 2005-06-08 NO NO20052781A patent/NO330983B1/no not_active IP Right Cessation
-
2009
- 2009-03-16 US US12/404,575 patent/US8273878B2/en not_active Expired - Fee Related
-
2010
- 2010-01-11 CY CY20101100025T patent/CY1110605T1/el unknown
- 2010-06-23 JP JP2010142779A patent/JP5318037B2/ja not_active Expired - Fee Related
-
2011
- 2011-03-10 NO NO20110366A patent/NO20110366L/no not_active Application Discontinuation
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| Date | Code | Title | Description |
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| RENW | Renewal (renewal fees accepted) | ||
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |