ZA200409881B - Pyrimidinone compounds compositions and methods - Google Patents

Pyrimidinone compounds compositions and methods Download PDF

Info

Publication number: ZA200409881B
Authority: ZA; South Africa
Prior art keywords: optionally substituted; alkyl; compound according; methyl; hydrogen
Prior art date: 2002-05-09

Application number

ZA200409881A

Other languages

English (en)

Inventor

Han-Jie Zhou

David J C Morgans Jr

Steven David Knight

Kenneth A Newlander

Dashyant Dhanak

Nicholas D Adams

Gustave Bergnes

Original Assignee

Cytokinetics Inc

Smithkline Beecham Corp

Priority date (The priority date 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 date listed.)

2002-05-09

Filing date

2004-12-07

Publication date

2006-04-26

2004-12-07 Application filed by Cytokinetics Inc, Smithkline Beecham Corp filed Critical Cytokinetics Inc

2006-04-26 Publication of ZA200409881B publication Critical patent/ZA200409881B/en

Links

239000000203 mixture Substances 0.000 title claims description 23
238000000034 method Methods 0.000 title claims description 20
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title description 2
-1 aminocarbonyl- Chemical group 0.000 claims description 314
150000001875 compounds Chemical class 0.000 claims description 104
229910052799 carbon Inorganic materials 0.000 claims description 103
125000000217 alkyl group Chemical group 0.000 claims description 96
229910052739 hydrogen Inorganic materials 0.000 claims description 45
239000001257 hydrogen Substances 0.000 claims description 42
125000001072 heteroaryl group Chemical group 0.000 claims description 38
125000000547 substituted alkyl group Chemical group 0.000 claims description 31
102000010638 Kinesin Human genes 0.000 claims description 30
108010063296 Kinesin Proteins 0.000 claims description 30
125000003107 substituted aryl group Chemical group 0.000 claims description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 27
239000012453 solvate Substances 0.000 claims description 20
125000003710 aryl alkyl group Chemical group 0.000 claims description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 11
230000000694 effects Effects 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
206010028980 Neoplasm Diseases 0.000 claims description 9
201000011510 cancer Diseases 0.000 claims description 9
230000001413 cellular effect Effects 0.000 claims description 9
125000004475 heteroaralkyl group Chemical group 0.000 claims description 9
230000002062 proliferating effect Effects 0.000 claims description 8
125000005415 substituted alkoxy group Chemical group 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
208000035475 disorder Diseases 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
230000002401 inhibitory effect Effects 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
125000005518 carboxamido group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
206010007572 Cardiac hypertrophy Diseases 0.000 claims description 5
208000006029 Cardiomegaly Diseases 0.000 claims description 5
206010061218 Inflammation Diseases 0.000 claims description 5
206010020718 hyperplasia Diseases 0.000 claims description 5
208000026278 immune system disease Diseases 0.000 claims description 5
230000004054 inflammatory process Effects 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
208000037803 restenosis Diseases 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
229940123237 Taxane Drugs 0.000 claims description 3
239000002246 antineoplastic agent Substances 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
229940122803 Vinca alkaloid Drugs 0.000 claims description 2
229940127089 cytotoxic agent Drugs 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 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
150000002431 hydrogen Chemical class 0.000 claims 16
238000004519 manufacturing process Methods 0.000 claims 6
101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
125000005059 halophenyl group Chemical group 0.000 claims 3
125000003944 tolyl group Chemical group 0.000 claims 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims 1
MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims 1
KJCWDNBRKFOJEC-UHFFFAOYSA-N 2-(3-carbamoylpyridin-2-yl)pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1C1=NC=CC=C1C(N)=O KJCWDNBRKFOJEC-UHFFFAOYSA-N 0.000 claims 1
RXEYIBXYCMOPLN-UHFFFAOYSA-N 2-[1-[4-(2-aminoethyl)-2-(4-methylphenyl)imidazol-1-yl]-2-methylpropyl]-3-benzyl-5,6-dimethylpyrimidin-4-one Chemical compound C1=C(CCN)N=C(C=2C=CC(C)=CC=2)N1C(C(C)C)C1=NC(C)=C(C)C(=O)N1CC1=CC=CC=C1 RXEYIBXYCMOPLN-UHFFFAOYSA-N 0.000 claims 1
BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 claims 1
TWJJJWVXSQMTJV-XMMPIXPASA-N 3-benzyl-5,6-dimethyl-2-[(1r)-2-methyl-1-[2-(4-methylphenyl)-4,5-dihydroimidazol-1-yl]propyl]pyrimidin-4-one Chemical compound N1([C@H](C(C)C)C=2N(C(=O)C(C)=C(C)N=2)CC=2C=CC=CC=2)CCN=C1C1=CC=C(C)C=C1 TWJJJWVXSQMTJV-XMMPIXPASA-N 0.000 claims 1
JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims 1
229940127007 Compound 39 Drugs 0.000 claims 1
229940123780 DNA topoisomerase I inhibitor Drugs 0.000 claims 1
101100134922 Gallus gallus COR5 gene Proteins 0.000 claims 1
239000000365 Topoisomerase I Inhibitor Substances 0.000 claims 1
125000004442 acylamino group Chemical group 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
125000003277 amino group Chemical group 0.000 claims 1
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
229940125904 compound 1 Drugs 0.000 claims 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 1
125000006399 methylpyrazinyl group Chemical group 0.000 claims 1
YEEPQJPOFGCJGV-SSEXGKCCSA-N n-(3-aminopropyl)-n-[(1r)-1-[1-benzyl-5-(3-chlorophenyl)-4-methyl-6-oxopyrimidin-2-yl]-2-methylpropyl]-4-methylbenzamide Chemical compound NCCCN([C@H](C(C)C)C=1N(C(=O)C(C=2C=C(Cl)C=CC=2)=C(C)N=1)CC=1C=CC=CC=1)C(=O)C1=CC=C(C)C=C1 YEEPQJPOFGCJGV-SSEXGKCCSA-N 0.000 claims 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
230000000394 mitotic effect Effects 0.000 description 27
125000003118 aryl group Chemical group 0.000 description 20
125000001188 haloalkyl group Chemical group 0.000 description 13
102000029749 Microtubule Human genes 0.000 description 10
108091022875 Microtubule Proteins 0.000 description 10
125000000623 heterocyclic group Chemical group 0.000 description 10
210000004688 microtubule Anatomy 0.000 description 10
125000005037 alkyl phenyl group Chemical group 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
229910052736 halogen Inorganic materials 0.000 description 8
150000002367 halogens Chemical class 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000003112 inhibitor Substances 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
125000000753 cycloalkyl group Chemical group 0.000 description 5
230000011278 mitosis Effects 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
101001008953 Homo sapiens Kinesin-like protein KIF11 Proteins 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000002927 anti-mitotic effect Effects 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000004663 cell proliferation Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
230000002538 fungal effect Effects 0.000 description 3
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
102000055595 human KIF11 Human genes 0.000 description 3
125000004043 oxo group Chemical group O=* 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
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
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 2
241001635598 Enicostema Species 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
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 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
206010027626 Milia Diseases 0.000 description 2
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
230000008901 benefit Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
230000030833 cell death Effects 0.000 description 2
239000000460 chlorine Chemical group 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000000392 cycloalkenyl group Chemical group 0.000 description 2
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000004064 dysfunction Effects 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000012634 fragment Substances 0.000 description 2
238000001030 gas--liquid chromatography Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
238000012216 screening Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000003831 tetrazolyl group Chemical group 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
125000000335 thiazolyl group Chemical group 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
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Classifications

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- C07D239/32—One oxygen, sulfur or nitrogen atom
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- 2003-05-02 BR BRPI0309892-3A patent/BR0309892A2/pt not_active IP Right Cessation
- 2003-05-02 RU RU2004135554/04A patent/RU2004135554A/ru unknown
- 2003-05-02 JP JP2004502928A patent/JP2006508030A/ja active Pending
- 2003-05-02 PL PL03373412A patent/PL373412A1/xx unknown
- 2003-05-02 CN CNB03816177XA patent/CN100491358C/zh not_active Expired - Fee Related
- 2003-05-02 KR KR1020047018077A patent/KR20050036911A/ko not_active Ceased
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- 2003-05-02 NZ NZ537076A patent/NZ537076A/en unknown
- 2003-05-02 EP EP03719989A patent/EP1503993A4/fr not_active Withdrawn
- 2003-05-02 US US10/429,195 patent/US7166595B2/en not_active Expired - Fee Related
- 2003-05-02 AU AU2003223786A patent/AU2003223786A1/en not_active Abandoned
- 2003-05-02 CA CA002485148A patent/CA2485148A1/fr not_active Abandoned
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- 2003-05-07 TW TW092112382A patent/TW200406387A/zh unknown
- 2003-05-08 AR ARP030101617A patent/AR039985A1/es unknown
2004
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- 2004-11-19 NO NO20045043A patent/NO20045043L/no not_active Application Discontinuation
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2006
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Publication number	Publication date
US20070135432A1 (en)	2007-06-14
CA2485148A1 (fr)	2003-11-20
EP1503993A2 (fr)	2005-02-09
IS7520A (is)	2004-11-03
CN1665788A (zh)	2005-09-07
CN100491358C (zh)	2009-05-27
EP1503993A4 (fr)	2006-05-03
MY140767A (en)	2010-01-15
NO20045043L (no)	2005-02-08
WO2003094839A2 (fr)	2003-11-20
TW200406387A (en)	2004-05-01
AR039985A1 (es)	2005-03-09
WO2003094839A3 (fr)	2004-09-16
US7482343B2 (en)	2009-01-27
JP2006508030A (ja)	2006-03-09
BR0309892A2 (pt)	2011-04-05
AU2003223786A1 (en)	2003-11-11
KR20050036911A (ko)	2005-04-20
MXPA04011074A (es)	2005-06-08
IL187528A0 (en)	2008-03-20
WO2003094839A8 (fr)	2004-06-24
US20040077662A1 (en)	2004-04-22
US7166595B2 (en)	2007-01-23
RU2004135554A (ru)	2006-01-20
NZ537076A (en)	2007-06-29
PL373412A1 (en)	2005-08-22
IL165046A0 (en)	2005-12-18

Publication	Publication Date	Title
ZA200409881B (en)	2006-04-26	Pyrimidinone compounds compositions and methods
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EP1622883A2 (fr)	2006-02-08	Composes, compositions, et procedes
WO2005013888A2 (fr)	2005-02-17	Composes, compositions et procedes