ES2314106T3 - Derivados de pirimidina, agentes farmaceuticos que contiene dichos compuestos, uso y metodo para su obtencion. - Google Patents
Derivados de pirimidina, agentes farmaceuticos que contiene dichos compuestos, uso y metodo para su obtencion. Download PDFInfo
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- ES2314106T3 ES2314106T3 ES02774710T ES02774710T ES2314106T3 ES 2314106 T3 ES2314106 T3 ES 2314106T3 ES 02774710 T ES02774710 T ES 02774710T ES 02774710 T ES02774710 T ES 02774710T ES 2314106 T3 ES2314106 T3 ES 2314106T3
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- Prior art keywords
- alkyl
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- 238000000034 method Methods 0.000 title claims description 443
- 150000001875 compounds Chemical class 0.000 title claims description 65
- 239000008177 pharmaceutical agent Substances 0.000 title description 2
- -1 aralkoxy Chemical group 0.000 claims abstract description 784
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 360
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 141
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 137
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 132
- 125000003118 aryl group Chemical group 0.000 claims abstract description 126
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 114
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 109
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 99
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 95
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 94
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 89
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 88
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 81
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 79
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 74
- 239000000460 chlorine Substances 0.000 claims abstract description 73
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 73
- 239000001301 oxygen Substances 0.000 claims abstract description 73
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 72
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 65
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 64
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 63
- 239000011737 fluorine Substances 0.000 claims abstract description 63
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 63
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 59
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 58
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 56
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 49
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 47
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 47
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 45
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 43
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 41
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 39
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract description 39
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 35
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 33
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 31
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims abstract description 29
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 27
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 26
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims abstract description 25
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims abstract description 25
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims abstract description 23
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims abstract description 17
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims abstract description 17
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 17
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims abstract description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 12
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 11
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims abstract description 11
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims abstract description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 9
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims abstract description 7
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 7
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 5
- 150000003230 pyrimidines Chemical class 0.000 claims abstract description 4
- 125000006413 ring segment Chemical group 0.000 claims abstract description 3
- 125000004429 atom Chemical group 0.000 claims description 156
- 125000002947 alkylene group Chemical group 0.000 claims description 84
- 125000004432 carbon atom Chemical group C* 0.000 claims description 84
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 76
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 50
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 47
- 239000011593 sulfur Substances 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 44
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 43
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 38
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 36
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 33
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 32
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 24
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 22
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 22
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 22
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 18
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 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 claims description 12
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 12
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 12
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 12
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 10
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 10
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 10
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 10
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 10
- 239000011630 iodine Substances 0.000 claims description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 8
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 8
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 6
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 4
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 4
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 230000004663 cell proliferation Effects 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
- 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 230000006806 disease prevention Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 241000790917 Dioxys <bee> Species 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 230000002159 abnormal effect Effects 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 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
- 150000003254 radicals Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 413
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33014501P | 2001-10-17 | 2001-10-17 | |
| US330145P | 2001-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2314106T3 true ES2314106T3 (es) | 2009-03-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ES02774710T Expired - Lifetime ES2314106T3 (es) | 2001-10-17 | 2002-10-14 | Derivados de pirimidina, agentes farmaceuticos que contiene dichos compuestos, uso y metodo para su obtencion. |
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| Country | Link |
|---|---|
| US (3) | US7173028B2 (enExample) |
| EP (3) | EP1438053B1 (enExample) |
| JP (1) | JP4460292B2 (enExample) |
| AT (1) | ATE407678T1 (enExample) |
| CA (1) | CA2463989C (enExample) |
| CY (1) | CY1110442T1 (enExample) |
| DE (1) | DE50212771D1 (enExample) |
| DK (1) | DK1438053T3 (enExample) |
| ES (1) | ES2314106T3 (enExample) |
| PT (1) | PT1438053E (enExample) |
| UY (1) | UY27487A1 (enExample) |
| WO (1) | WO2003032997A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2365960A1 (es) * | 2010-03-31 | 2011-10-14 | Palobiofarma, S.L | Nuevos antagonistas de los receptores de adenosina. |
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-
2002
- 2002-10-14 DE DE50212771T patent/DE50212771D1/de not_active Expired - Lifetime
- 2002-10-14 EP EP02774710A patent/EP1438053B1/de not_active Expired - Lifetime
- 2002-10-14 DK DK02774710T patent/DK1438053T3/da active
- 2002-10-14 JP JP2003535800A patent/JP4460292B2/ja not_active Expired - Lifetime
- 2002-10-14 UY UY27487A patent/UY27487A1/es not_active Application Discontinuation
- 2002-10-14 CA CA2463989A patent/CA2463989C/en not_active Expired - Lifetime
- 2002-10-14 PT PT02774710T patent/PT1438053E/pt unknown
- 2002-10-14 EP EP10178604A patent/EP2332924A1/de not_active Withdrawn
- 2002-10-14 EP EP08163784A patent/EP2090571B1/de not_active Expired - Lifetime
- 2002-10-14 WO PCT/EP2002/011453 patent/WO2003032997A1/de not_active Ceased
- 2002-10-14 AT AT02774710T patent/ATE407678T1/de active
- 2002-10-14 ES ES02774710T patent/ES2314106T3/es not_active Expired - Lifetime
- 2002-10-16 US US10/271,763 patent/US7173028B2/en not_active Expired - Lifetime
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2005
- 2005-12-21 US US11/313,380 patent/US7709480B2/en not_active Expired - Lifetime
-
2008
- 2008-12-02 CY CY20081101391T patent/CY1110442T1/el unknown
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2010
- 2010-02-24 US US12/711,364 patent/US8420630B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2365960A1 (es) * | 2010-03-31 | 2011-10-14 | Palobiofarma, S.L | Nuevos antagonistas de los receptores de adenosina. |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2332924A1 (de) | 2011-06-15 |
| US8420630B2 (en) | 2013-04-16 |
| UY27487A1 (es) | 2003-05-30 |
| WO2003032997A1 (de) | 2003-04-24 |
| EP1438053B1 (de) | 2008-09-10 |
| CA2463989A1 (en) | 2003-04-24 |
| EP2090571B1 (de) | 2012-05-16 |
| EP1438053A1 (de) | 2004-07-21 |
| US7173028B2 (en) | 2007-02-06 |
| ATE407678T1 (de) | 2008-09-15 |
| JP2005509624A (ja) | 2005-04-14 |
| EP2090571A1 (de) | 2009-08-19 |
| DK1438053T3 (da) | 2008-12-08 |
| US7709480B2 (en) | 2010-05-04 |
| DE50212771D1 (de) | 2008-10-23 |
| CA2463989C (en) | 2012-01-31 |
| PT1438053E (pt) | 2008-09-25 |
| JP4460292B2 (ja) | 2010-05-12 |
| US20030171359A1 (en) | 2003-09-11 |
| US20060100211A1 (en) | 2006-05-11 |
| CY1110442T1 (el) | 2015-04-29 |
| US20100152167A1 (en) | 2010-06-17 |
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