HRP20100724T1 - Supstituirani biciklički derivati pirimidona - Google Patents
Supstituirani biciklički derivati pirimidona Download PDFInfo
- Publication number
- HRP20100724T1 HRP20100724T1 HR20100724T HRP20100724T HRP20100724T1 HR P20100724 T1 HRP20100724 T1 HR P20100724T1 HR 20100724 T HR20100724 T HR 20100724T HR P20100724 T HRP20100724 T HR P20100724T HR P20100724 T1 HRP20100724 T1 HR P20100724T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyrimidin
- oxo
- benzamide
- pyrido
- tetrahydro
- Prior art date
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- -1 bicyclic pyrimidone derivatives Chemical class 0.000 title claims abstract 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 19
- 125000005843 halogen group Chemical group 0.000 claims abstract 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 8
- 150000008318 pyrimidones Chemical class 0.000 claims abstract 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 7
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 239000012453 solvate Substances 0.000 claims abstract 7
- 125000001424 substituent group Chemical group 0.000 claims abstract 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 5
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract 3
- 125000003277 amino group Chemical group 0.000 claims abstract 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 3
- 125000004754 (C2-C12) dialkylamino group Chemical group 0.000 claims abstract 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims abstract 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- CKUWDKIWOWBWQX-UHFFFAOYSA-N 4-chloro-2-methoxy-n-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)benzamide Chemical compound COC1=CC(Cl)=CC=C1C(=O)NC1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCC1 CKUWDKIWOWBWQX-UHFFFAOYSA-N 0.000 claims 3
- DFDIIRFPDVASFL-UHFFFAOYSA-N 4-chloro-2-methoxy-n-(4-oxo-2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepin-10-yl)benzamide Chemical compound COC1=CC(Cl)=CC=C1C(=O)NC1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCCC1 DFDIIRFPDVASFL-UHFFFAOYSA-N 0.000 claims 3
- GGSDBBMBCWCUNI-UHFFFAOYSA-N 4-chloro-2-methoxy-n-(9-methyl-4-oxo-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrido[1,2-a]pyrimidin-9-yl)benzamide Chemical compound COC1=CC(Cl)=CC=C1C(=O)NC1(C)C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCC1 GGSDBBMBCWCUNI-UHFFFAOYSA-N 0.000 claims 3
- INSTULVJFXPJIN-UHFFFAOYSA-N 4-fluoro-2-methoxy-n-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)benzamide Chemical compound COC1=CC(F)=CC=C1C(=O)NC1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCC1 INSTULVJFXPJIN-UHFFFAOYSA-N 0.000 claims 3
- XANTUAVSKYBKQG-UHFFFAOYSA-N 4-fluoro-2-methoxy-n-(4-oxo-2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepin-10-yl)benzamide Chemical compound COC1=CC(F)=CC=C1C(=O)NC1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCCC1 XANTUAVSKYBKQG-UHFFFAOYSA-N 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 230000003449 preventive effect Effects 0.000 claims 3
- 230000001225 therapeutic effect Effects 0.000 claims 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- WIJDTWWDWDIGOA-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)urea Chemical compound C1=CC(F)=CC=C1NC(=O)NC1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCC1 WIJDTWWDWDIGOA-UHFFFAOYSA-N 0.000 claims 1
- XFIYYWMVQUBRQQ-UHFFFAOYSA-N 1-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1CCCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 XFIYYWMVQUBRQQ-UHFFFAOYSA-N 0.000 claims 1
- KTCHPIKUCFMRMN-UHFFFAOYSA-N 2-chloro-4-fluoro-5-nitro-n-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)benzamide Chemical compound C1=C(F)C([N+](=O)[O-])=CC(C(=O)NC2C=3N(C(C=C(N=3)C=3C=CN=CC=3)=O)CCC2)=C1Cl KTCHPIKUCFMRMN-UHFFFAOYSA-N 0.000 claims 1
- BLSSPZDFXCZISN-UHFFFAOYSA-N 2-chloro-5-fluoro-n-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)benzamide Chemical compound FC1=CC=C(Cl)C(C(=O)NC2C=3N(C(C=C(N=3)C=3C=CN=CC=3)=O)CCC2)=C1 BLSSPZDFXCZISN-UHFFFAOYSA-N 0.000 claims 1
- RTTJPVMNLVDCCY-UHFFFAOYSA-N 2-fluoro-6-methoxy-n-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)benzamide Chemical compound COC1=CC=CC(F)=C1C(=O)NC1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCC1 RTTJPVMNLVDCCY-UHFFFAOYSA-N 0.000 claims 1
- MRSSEAKGSAQVNN-UHFFFAOYSA-N 2-fluoro-6-methoxy-n-(9-methyl-4-oxo-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrido[1,2-a]pyrimidin-9-yl)benzamide Chemical compound COC1=CC=CC(F)=C1C(=O)NC1(C)C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCC1 MRSSEAKGSAQVNN-UHFFFAOYSA-N 0.000 claims 1
- PNGVAKSZAFTOCU-UHFFFAOYSA-N 2-methoxy-n-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)-4-(trifluoromethyl)benzamide Chemical compound COC1=CC(C(F)(F)F)=CC=C1C(=O)NC1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCC1 PNGVAKSZAFTOCU-UHFFFAOYSA-N 0.000 claims 1
- OJBGSHCXUDLIIU-UHFFFAOYSA-N 2-methoxy-n-(4-oxo-2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepin-10-yl)-5-(trifluoromethoxy)benzamide Chemical compound COC1=CC=C(OC(F)(F)F)C=C1C(=O)NC1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCCC1 OJBGSHCXUDLIIU-UHFFFAOYSA-N 0.000 claims 1
- AIIAVPCFVMSRGR-UHFFFAOYSA-N 2-methoxy-n-(9-methyl-4-oxo-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrido[1,2-a]pyrimidin-9-yl)-4-(trifluoromethyl)benzamide Chemical compound COC1=CC(C(F)(F)F)=CC=C1C(=O)NC1(C)C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCC1 AIIAVPCFVMSRGR-UHFFFAOYSA-N 0.000 claims 1
- BQBQKGNDPDUHGJ-UHFFFAOYSA-N 2-methoxy-n-(9-methyl-4-oxo-2-pyrimidin-4-yl-7,8-dihydro-6h-pyrido[1,2-a]pyrimidin-9-yl)benzamide Chemical compound COC1=CC=CC=C1C(=O)NC1(C)C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCC1 BQBQKGNDPDUHGJ-UHFFFAOYSA-N 0.000 claims 1
- SEPGRBDYAPSYOM-UHFFFAOYSA-N 4-amino-2-methoxy-n-(4-oxo-2-pyridin-4-yl-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepin-10-yl)benzamide Chemical compound COC1=CC(N)=CC=C1C(=O)NC1C2=NC(C=3C=CN=CC=3)=CC(=O)N2CCCC1 SEPGRBDYAPSYOM-UHFFFAOYSA-N 0.000 claims 1
- FCZXIQQVNDHACY-UHFFFAOYSA-N 4-amino-2-methoxy-n-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)benzamide Chemical compound COC1=CC(N)=CC=C1C(=O)NC1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCC1 FCZXIQQVNDHACY-UHFFFAOYSA-N 0.000 claims 1
- KTQAQRKEPFLAOH-UHFFFAOYSA-N 4-amino-2-methoxy-n-(4-oxo-2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6h-pyrimido[1,2-a]azepin-10-yl)benzamide Chemical compound COC1=CC(N)=CC=C1C(=O)NC1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCCC1 KTQAQRKEPFLAOH-UHFFFAOYSA-N 0.000 claims 1
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- VEFFVCNCLXVCRP-UHFFFAOYSA-N n-(3-bromo-4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC1C2=NC(C=3C=CN=CC=3)=C(Br)C(=O)N2CCC1 VEFFVCNCLXVCRP-UHFFFAOYSA-N 0.000 claims 1
- OONSEEILRXGKJY-UHFFFAOYSA-N n-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)-2-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=CC=C1C(=O)NC1C2=NC(C=3C=CN=CC=3)=CC(=O)N2CCC1 OONSEEILRXGKJY-UHFFFAOYSA-N 0.000 claims 1
- MSUWKVCCPLTSBI-UHFFFAOYSA-N n-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)-2-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)NC1C2=NC(C=3C=CN=CC=3)=CC(=O)N2CCC1 MSUWKVCCPLTSBI-UHFFFAOYSA-N 0.000 claims 1
- HMJUGLYFKIHSHX-UHFFFAOYSA-N n-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)-2-phenylacetamide Chemical compound C1CCN(C(C=C(N=2)C=3C=CN=CC=3)=O)C=2C1NC(=O)CC1=CC=CC=C1 HMJUGLYFKIHSHX-UHFFFAOYSA-N 0.000 claims 1
- PXMBPBFPOFGQNM-UHFFFAOYSA-N n-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)naphthalene-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NC1CCCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 PXMBPBFPOFGQNM-UHFFFAOYSA-N 0.000 claims 1
- FYIPSSRLXWSJPT-UHFFFAOYSA-N n-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1CCCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 FYIPSSRLXWSJPT-UHFFFAOYSA-N 0.000 claims 1
- NZGIIAXAUXHAFV-UHFFFAOYSA-N n-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)naphthalene-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NC1CCCN(C(C=2)=O)C1=NC=2C1=CC=NC=N1 NZGIIAXAUXHAFV-UHFFFAOYSA-N 0.000 claims 1
- 208000004235 neutropenia Diseases 0.000 claims 1
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- PVIYWNGDTZSYHI-UHFFFAOYSA-N phenyl n-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl)carbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1CCCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 PVIYWNGDTZSYHI-UHFFFAOYSA-N 0.000 claims 1
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- 239000000126 substance Substances 0.000 claims 1
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Abstract
Derivat pirimidona prikazan formulom (I), ili njegova sol, ili njegov solvat ili njegov hidrat: naznačen time što: Y predstavlja dva atoma vodika, atom sumpora, atom kisika ili C1-2 alkilnu skupinu i atom vodika; Z predstavlja vezu, atom kisika, atom dušika, supstituiran atomom vodika ili C1-3 alkilnom skupinom, atom sumpora, metilensku skupinu, izborno supstituiranu s jednom ili dvije skupine, koje se bira između C1-6 alkilne skupine, hidroksilne skupine, C1-6 alkoksi skupine, C1-2 perhalogenirane alkilne skupina ili amino skupine; R1 predstavlja 2-, 3- ili 4-piridinski prsten ili 2-, 4- ili 5-pirimidinski prsten, gdje je navedeni prsten izborno supstituiran s C1-6 alkilnom skupinom, C1-6 alkoksi skupinom ili atomom halogena; R2 predstavlja benzenski prsten ili naftalenski prsten, gdje su navedeni prsteni izborno supstituirani s 1 do 4 supstituenta, koje se bira između C1-6 alkilne skupine, C3-7 cikloalkilne skupine, C3-7 cikloalkil-C1-6 alkilne skupine, atoma halogena, C1-2 perhalogenirane alkilne skupine, C1-3 halogenirane alkilne skupine, hidroksilne skupine, C1-6 alkoksi skupine, izborno supstituirane s C3-5 cikloalkilnom skupinom, C1-2 perhalogeniranom alkoksi skupinom, C1-6 alkilsulfonilnom skupinom, nitro, cijano, amino, C1-6 monoalkilamino skupinom, C2-12 dialkilamino skupinom, acetoksi skupinom ili aminosulfonilnom skupinom; R3 predstavlja atom vodika, C1-6 alkilnu skupinu ili atom halogena; R4 predstavlja atom vodika ili C1-6 alkilnu skupinu; R5 predstavlja atom vodika, C1-6 alkilnu skupinu, izborno supstituiranu s 1 do 4 supstituenta, koje se bira između atoma halogena, fenilne skupine, hidroksilne skupine ili C1-6 alkoksi skupine; R6 predstavlja atom vodika, C1-6 alkilnu skupinu ili atom halogena; R7 predstavlja atom vodika ili C1-6 alkilnu skupinu; in predstavlja 0 do 3; m predstavlja 0 do 1; o predstavlja 0 do 2. Patent sadrži još 13 patentnih zahtjeva.
Claims (14)
1. Derivat pirimidona prikazan formulom (I), ili njegova sol, ili njegov solvat ili njegov hidrat:
[image]
naznačen time što:
Y predstavlja dva atoma vodika, atom sumpora, atom kisika ili C1-2 alkilnu skupinu i atom vodika;
Z predstavlja vezu, atom kisika, atom dušika, supstituiran atomom vodika ili C1-3 alkilnom skupinom, atom sumpora, metilensku skupinu, izborno supstituiranu s jednom ili dvije skupine, koje se bira između C1-6 alkilne skupine, hidroksilne skupine, C1-6 alkoksi skupine, C1-2 perhalogenirane alkilne skupina ili amino skupine;
R1 predstavlja 2-, 3- ili 4-piridinski prsten ili 2-, 4- ili 5-pirimidinski prsten, gdje je navedeni prsten izborno supstituiran s C1-6 alkilnom skupinom, C1-6 alkoksi skupinom ili atomom halogena;
R2 predstavlja benzenski prsten ili naftalenski prsten, gdje su navedeni prsteni izborno supstituirani s 1 do 4 supstituenta, koje se bira između C1-6 alkilne skupine, C3-7 cikloalkilne skupine, C3-7 cikloalkil-C1-6 alkilne skupine, atoma halogena, C1-2 perhalogenirane alkilne skupine, C1-3 halogenirane alkilne skupine, hidroksilne skupine, C1-6 alkoksi skupine, izborno supstituirane s C3-5 cikloalkilnom skupinom, C1-2 perhalogeniranom alkoksi skupinom, C1-6 alkilsulfonilnom skupinom, nitro, cijano, amino, C1-6 monoalkilamino skupinom, C2-12 dialkilamino skupinom, acetoksi skupinom ili aminosulfonilnom skupinom;
R3 predstavlja atom vodika, C1-6 alkilnu skupinu ili atom halogena;
R4 predstavlja atom vodika ili C1-6 alkilnu skupinu;
R5 predstavlja atom vodika, C1-6 alkilnu skupinu, izborno supstituiranu s 1 do 4 supstituenta, koje se bira između atoma halogena, fenilne skupine, hidroksilne skupine ili C1-6 alkoksi skupine;
R6 predstavlja atom vodika, C1-6 alkilnu skupinu ili atom halogena;
R7 predstavlja atom vodika ili C1-6 alkilnu skupinu; i
n predstavlja 0 do 3;
m predstavlja 0 do 1;
o predstavlja 0 do 2.
2. Derivat pirimidona, ili njegova sol, ili njegov solvat ili njegov hidrat, u skladu s patentnim zahtjevom 1, naznačen time što R1 predstavlja nesupstituirani 4-piridinski prsten ili nesupstituirani 4-pirimidinski prsten.
3. Derivat pirimidona, ili njegova sol, ili njegov solvat ili njegov hidrat, u skladu s patentnim zahtjevom 1, naznačen time što:
R1 predstavlja 3- ili 4-piridinski prsten, ili 4- ili 5-pirimidinski prsten, gdje je navedeni prsten izborno supstituiran s C1-2 alkilnom skupinom, C1-2 alkoksi skupinom ili atomom halogena;
R2 predstavlja benzenski prsten ili naftalenski prsten, gdje su navedeni prsteni izborno supstituirani s 1 do 4 supstituenta, koje se bira između C1-3 alkilne skupine, C3-5 cikloalkilne skupine, C3-5 cikloalkil-C1-4 alkilne skupine, atoma halogena, C1-3 halogenirane alkilne skupine, hidroksilne skupine, C1-3 alkoksi skupine, izborno supstituirane s C3-5 cikloalkilnom skupinom, C1-2 perhalogeniranom alkoksi skupinom, C1-6 alkilsulfonilnom skupina, nitro, cijano, amino, C1-3 monoalkilamino skupinom ili C2-6 dialkilamino skupinom;
R3 predstavlja atom vodika, C1-3 alkilnu skupinu ili atom halogena;
R4 predstavlja atom vodika ili C1-3 alkilna skupina;
R5 predstavlja atom vodika, C1-3 alkoksi karbonilnu skupinu ili C1-3 alkilnu skupinu, izborno supstituiranu s 1 do 4 supstituenta, koje se bira između atoma halogena, fenilne skupine, hidroksilne skupine ili C1-3 alkoksi skupina;
R6 predstavlja atom vodika, C1-3 alkilnu skupinu ili atom halogena;
R7 predstavlja atom vodika ili C1-3 alkilnu skupinu;
Y predstavlja dva atoma vodika, atom kisika ili C1-2 alkilnu skupinu i atom vodika;
Z predstavlja vezu, atom kisika, atom dušika, supstituiran atomom vodika ili C1-3 alkilnom skupinom, metilensku skupinu, izborno supstituiranu s jednom ili dvije skupine, koje se bira između C1-3 alkilne skupine, hidroksilne skupine, C1-3 alkoksi skupine, C1-2 perhalogenirane alkilne skupine ili amino skupine;
n predstavlja 0 do 3;
m predstavlja 0 do 1; i
o predstavlja 1 do 2.
4. Derivat pirimidona, ili njegova sol, ili njegov solvat ili njegov hidrat, u skladu s patentnim zahtjevom 1, naznačen time što:
R1 predstavlja nesupstituirani 4-piridinski prsten ili 4-pirimidinski prsten;
R2 predstavlja benzenski ili naftalenski prsten, gdje je navedeni prsten izborno supstituiran s 1 do 4 supstituenta, koje se bira između C1-3 alkilne skupine, C1-2 perhalogenirane alkilne skupine, C3-4 cikloalkilne skupine, C3-4 cikloalkil-C1-3 alkilne skupine, atoma halogena, hidroksilne skupine, nitro, cijano, amino, C1-3 alkoksi skupine, izborno supstituirane s C3-4 cikloalkilnom skupinom, C1-2 perhalogeniranom alkoksi skupinom ili C1-3 alkilsulfonilnom skupinom;
R3 predstavlja atom vodika ili atom halogena;
R4 predstavlja atom vodika;
R5 predstavlja atom vodika;
R6 predstavlja atom vodika, C1-6 alkilnu skupinu;
R7 predstavlja atom vodika;
Y predstavlja dva atoma vodika ili atom kisika;
Z predstavlja vezu, atom kisika, atom dušika, supstituiran atomom vodika;
n predstavlja 0 do 1;
m predstavlja 0 do 1; i
o predstavlja 1 do 2.
5. Derivat pirimidona prikazan formulom (III)
[image]
naznačen time što R1, R2, R3, R4, R5, R6, R7, m i o su definirani kao za spoj formule (I), u skladu s patentnim zahtjevom 1.
6. Derivat pirimidona, ili njegova sol, ili njegov solvat ili njegov hidrat, u skladu s patentnim zahtjevom 1, naznačen time što ga se bira iz skupine koju čine:
• (±)-N-(4-Okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-Metoksi-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-N-(4-Okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)-2-fenilacetamid
• (±)-Fenil-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)karbamat
• (±)-N-(4-Fluorfenil)-N'-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)urea
• (±)-N-(4-Okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)-N'-fenilurea
• (±)-9-[(2-Metoksibenzil)amino]-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-4-on
• (±)-3-Fluor-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Izopropoksi-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-Klor-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Fluor-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-3-Cijano-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-Klor-5-fluor-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-Metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Fluor-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)-2-(trifluormetil)benzamid
• (±)-4-Metoksi-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)-3-(trifluormetil)benzamid
• (±)-N-(4-Okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)-2-(trifluormetil)benzamid
• (±)-2-Klor-4-fluor-5-nitro-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-N-(4-Okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)-2-naftamid
• (±)-3-Klor-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2,6-Dimetoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-3-Metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-Fluor-6-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Fluor-2-metoksi-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-Etoksi-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-N-(3-Brom-4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)-2-metoksibenzamid
• (±)-4-Amino-5-klor-2-metoksi-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-N-(4-Okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)-2-(trifluormetoksi)benzamid
• (±)-2-Izopropoksi-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-(Ciklopropilmetoksi)-N-(4-okso-2-piridin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Amino-5-klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Fluor-2-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-(Ciklopropilmetoksi)-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-N-(4-Okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)-2-naftamid
• (±)-3-Klor-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-5-Klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Amino-2-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-Metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)-4-trifluormetilbenzamid
• (±)5-(Etilsulfonil)-2-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2,3-Dimetoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (–)-4-Klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (+)-4-Klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-5-Brom-2-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-{[(4-Okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)amino]karbonil}fenil-acetat
• (±)-2-Hidroksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Klor-2-metoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (+)-4-Klor-2-metoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (–)-4-Klor-2-metoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Klor-2-metoksi-N-metil-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (+)-4-Fluor-2-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (–)-4-Fluor-2-metoksi-N-(4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-5-Klor-2-metoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Fluor-2-metoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Amino-5-klor-2-metoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-Metoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)-4-trifluormetilbenzamid
• (±)-2-Fluor-6-metoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2-Metoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-5-Brom-2-metoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Dimetilamino-2-metoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-2,4-Dimetoksi-N-(9-metil-4-okso-2-pirimidin-4-il-6,7,8,9-tetrahidro-4H-pirido[1,2-a]pirimidin-9-il)benzamid
• (±)-4-Klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8-tetrahidropirolo[1,2-a]pirimidin-8-il)benzamid
• (±)-4-Fluor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8-tetrahidropirolo[1,2-a]pirimidin-8-il)benzamid
• (±)-4-Amino-5-klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8-tetrahidropirolo[1,2-a]pirimidin-8-il)benzamid
• (±)-5-Klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8-tetrahidropirolo[1,2-a]pirimidin-8-il)benzamid
• (±)-4-Klor-2-metoksi-N-(4-okso-2-piridin-4-il-4,6,7,8-tetrahidropirolo[1,2-a]pirimidin-8-il)benzamid
• (±)-4-Fluor-2-metoksi-N-(4-okso-2-piridin-4-il-4,6,7,8-tetrahidropirolo[1,2-a]pirimidin-8-il)benzamid
• (±)-4-Klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-4-Fluor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-5-Klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-4-Amino-5-klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-4-Amino-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-2-Metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-5-(Aminosulfonil)-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-2-Hidroksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-5-Brom-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-2,4-Dimetoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-2-{[(4-Okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)amino]karbonil}fenil-acetat
• (±)-2,3-Dimetoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-2-Metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)-5-(trifluormetoksi)benzamid
• (±)-2,5-Dimetoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (+)-4-Fluor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (–)-4-Fluor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-4-Klor-2-metoksi-N-(4-okso-2-piridin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-5-Brom-2-metoksi-N-(4-okso-2-piridin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-4-Fluor-2-metoksi-N-(4-okso-2-piridin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-2-Metoksi-N-(4-okso-2-piridin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-5-Klor-2-metoksi-N-(4-okso-2-piridin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-4-Amino-2-metoksi-N-(4-okso-2-piridin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (±)-2-{[(4-Okso-2-piridin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)amino]karbonil}fenil-acetat
• (±)-2,4-Dimetoksi-N-(4-okso-2-piridin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (+)-4-Klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid
• (–)-4-Klor-2-metoksi-N-(4-okso-2-pirimidin-4-il-4,6,7,8,9,10-heksahidropirimido[1,2-a]azepin-10-il)benzamid.
7. Medikament, naznačen time što kao aktivni sastojak sadrži tvar koju se bira iz skupine koju čine derivat pirimidona prikazan formulom (I), ili njegove soli, ili njegov solvat ili njegov hidrat, u skladu s patentnim zahtjevom 1.
8. Upotreba spoja u skladu s patentnim zahtjevima 1 do 3, naznačena time što je navedni spoj namijenjen pripravi medikamenta za preventivno i/ili terapijsko liječenje bolesti uzrokovane abnormalnom aktivnošću GSK3β.
9. Upotreba spoja u skladu s patentnim zahtjevima 1 do 3, naznačena time što je navedni spoj namijenjen pripravi medikamenta za preventivno i/ili terapijsko liječenje neurodegenerativne bolesti.
10. Upotreba spoja u skladu s patentnim zahtjevom 9, naznačena time što neurodegenerativnu bolest se bira iz skupine koju čine Alzheimerova bolest, Parkinsonova bolest, tauopatije, Wilsonova bolest, Huntingtonova bolest, prionska bolest, vaskularna demencija, akutni inzult, traumatske ozljede, cerebrovaskularna kap, ozljeda mozga, ozljeda kralježnične moždine, amiotrofna lateralna skleroza, periferne neuropatije, retinopatije ili glaukom.
11. Upotreba spoja u skladu s patentnim zahtjevima 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta za preventivno i/ili terapijsko liječenje dijabetesa neovisnog o inzulinu, pretilosti, malarije, bipolarnih poremećaja, shizofrenije, osteoporoze, alopecije ili raka.
12. Upotreba u skladu s patentnim zahtjevom 11, naznačena time što rak je rak dojke, karcinom velikih stanica pluća, rak štitnjače, Leukemija T- ili B-stanica ili tumori uzrokovani virusima.
13. Upotreba spoja u skladu s patentnim zahtjevima 1 do 3, naznačena time što je navedni spoj namijenjen pripravi medikamenta za liječenje ili sprječavanje pemphigus vulgaris (pemfigus).
14. Upotreba spoja u skladu s patentnim zahtjevima 1 do 3, naznačena time što je navedni spoj namijenjen pripravi medikamenta za liječenje neutropenije uzrokovane kemoterapijom raka.
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EP05292457A EP1790649A1 (en) | 2005-11-21 | 2005-11-21 | Substituted bicyclic pyrimidone derivatives |
PCT/IB2006/004046 WO2007057790A2 (en) | 2005-11-21 | 2006-11-21 | Substituted bicyclic pyrimidone derivatives |
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EP (2) | EP1790649A1 (hr) |
JP (1) | JP5124471B2 (hr) |
KR (1) | KR20080070671A (hr) |
CN (1) | CN101312971B (hr) |
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AT (1) | ATE487718T1 (hr) |
BR (1) | BRPI0618752A2 (hr) |
CA (1) | CA2630360A1 (hr) |
CY (1) | CY1111125T1 (hr) |
DE (1) | DE602006018190D1 (hr) |
DK (1) | DK1957492T3 (hr) |
EA (1) | EA014918B1 (hr) |
ES (1) | ES2355756T3 (hr) |
HK (1) | HK1126204A1 (hr) |
HR (1) | HRP20100724T1 (hr) |
IL (1) | IL191213A (hr) |
MX (1) | MX2008006321A (hr) |
NZ (1) | NZ568014A (hr) |
PL (1) | PL1957492T3 (hr) |
PT (1) | PT1957492E (hr) |
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SI (1) | SI1957492T1 (hr) |
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EP1992621A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Heteroarylamide-substituted pyrimidone derivatives for the treatment of neurodegenerative diseases |
EP1992624A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Heteroarylamide pyrimidone compounds |
EP1992625A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Arylamide pyrimidone compounds |
EP1992620A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Arylamide pyrimidone derivatives for the treatment of neurodegenerative diseases |
EP2085400A1 (en) | 2008-01-29 | 2009-08-05 | Sanofi-Aventis | Substituted heteroarylamide oxazepinopyrimidone derivatives |
EP2090578A1 (en) * | 2008-01-29 | 2009-08-19 | Sanofi-Aventis | Substituted arylamide diazepinopyrimidone derivatives for the treatment of neurodegenerative diseases caused by abnormal activity of GSK3-beta |
EP2085399A1 (en) | 2008-01-29 | 2009-08-05 | Sanofi-Aventis | substituted arylamide oxazepinopyrimidone derivatives |
EP2090579A1 (en) * | 2008-01-29 | 2009-08-19 | Sanofi-Aventis | Substituted heteroarylamide diazepinopyrimidone derivatives |
EP2138492A1 (en) * | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted pyrimidin-4-one derivatives |
EP2138485A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted N-Oxide pyrazine derivatives |
EP2138488A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | 4-(pyridin-4-yl)-1H-[1,3,5]triazin-2-one derivatives as GSK3-beta inhibitors for the treatment of neurodegenerative diseases |
EP2138495A1 (en) * | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted pyrimido[2,1-a]isoquinolin-4-one derivatives |
EP2138493A1 (en) * | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted pyrimidone derivatives |
EP2138498A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted tricyclic derivatives against neurodegenerative diseases |
EP2138494A1 (en) * | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted alkyl pyrimidin-4-one derivatives |
JP7250687B2 (ja) | 2017-10-06 | 2023-04-03 | 武田薬品工業株式会社 | 複素環化合物 |
EP3693368B1 (en) * | 2017-10-06 | 2023-12-06 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
CN109748914B (zh) * | 2018-12-29 | 2021-05-25 | 上海珂臻医药科技有限公司 | 吡啶并嘧啶类化合物及其应用 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU178496B (en) * | 1977-12-29 | 1982-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing 6,7,8,9-tetrahydro-4h-pyrido/1,2-a/pyrimidine derivatives with antiallergic activity |
DE60022388T2 (de) * | 1999-12-17 | 2006-06-14 | Chiron Corp | Bizyklische inhibitoren von glycogensynthasekinase 3 |
EP1460076A1 (en) * | 2003-03-21 | 2004-09-22 | Sanofi-Synthelabo | Substituted 8-perfluoroalkyl-6,7,8,9-tetrahydropyrimido[1,2-a] pyrimidin-4-one derivatives |
JO2985B1 (ar) * | 2006-12-20 | 2016-09-05 | Takeda Pharmaceuticals Co | مثبطات كينازmapk/erk |
-
2005
- 2005-11-21 EP EP05292457A patent/EP1790649A1/en not_active Withdrawn
-
2006
- 2006-11-12 ZA ZA200804335A patent/ZA200804335B/xx unknown
- 2006-11-17 AR ARP060105057A patent/AR057906A1/es not_active Application Discontinuation
- 2006-11-21 ES ES06847275T patent/ES2355756T3/es active Active
- 2006-11-21 PL PL06847275T patent/PL1957492T3/pl unknown
- 2006-11-21 EP EP06847275A patent/EP1957492B1/en active Active
- 2006-11-21 BR BRPI0618752-8A patent/BRPI0618752A2/pt not_active IP Right Cessation
- 2006-11-21 NZ NZ568014A patent/NZ568014A/en not_active IP Right Cessation
- 2006-11-21 EA EA200801134A patent/EA014918B1/ru not_active IP Right Cessation
- 2006-11-21 CN CN2006800435223A patent/CN101312971B/zh not_active Expired - Fee Related
- 2006-11-21 CA CA002630360A patent/CA2630360A1/en not_active Abandoned
- 2006-11-21 JP JP2008540723A patent/JP5124471B2/ja not_active Expired - Fee Related
- 2006-11-21 KR KR1020087012084A patent/KR20080070671A/ko not_active Application Discontinuation
- 2006-11-21 RS RS20110055A patent/RS51654B/en unknown
- 2006-11-21 WO PCT/IB2006/004046 patent/WO2007057790A2/en active Application Filing
- 2006-11-21 SI SI200630901T patent/SI1957492T1/sl unknown
- 2006-11-21 AT AT06847275T patent/ATE487718T1/de active
- 2006-11-21 PT PT06847275T patent/PT1957492E/pt unknown
- 2006-11-21 MX MX2008006321A patent/MX2008006321A/es active IP Right Grant
- 2006-11-21 DE DE602006018190T patent/DE602006018190D1/de active Active
- 2006-11-21 DK DK06847275.2T patent/DK1957492T3/da active
-
2008
- 2008-05-01 IL IL191213A patent/IL191213A/en not_active IP Right Cessation
- 2008-05-16 US US12/122,111 patent/US8148364B2/en not_active Expired - Fee Related
-
2009
- 2009-05-22 HK HK09104689.9A patent/HK1126204A1/xx not_active IP Right Cessation
-
2010
- 2010-12-27 HR HR20100724T patent/HRP20100724T1/hr unknown
-
2011
- 2011-01-21 CY CY20111100069T patent/CY1111125T1/el unknown
- 2011-08-03 US US13/197,228 patent/US20110294786A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
ES2355756T3 (es) | 2011-03-30 |
CA2630360A1 (en) | 2007-05-24 |
PT1957492E (pt) | 2011-01-24 |
DK1957492T3 (da) | 2011-02-28 |
CN101312971B (zh) | 2011-09-07 |
AR057906A1 (es) | 2007-12-26 |
DE602006018190D1 (de) | 2010-12-23 |
IL191213A (en) | 2012-02-29 |
JP5124471B2 (ja) | 2013-01-23 |
KR20080070671A (ko) | 2008-07-30 |
US20110294786A1 (en) | 2011-12-01 |
EA200801134A1 (ru) | 2009-02-27 |
SI1957492T1 (sl) | 2011-02-28 |
PL1957492T3 (pl) | 2011-04-29 |
EP1790649A1 (en) | 2007-05-30 |
US20090036427A1 (en) | 2009-02-05 |
ATE487718T1 (de) | 2010-11-15 |
EA014918B1 (ru) | 2011-04-29 |
JP2009516676A (ja) | 2009-04-23 |
EP1957492B1 (en) | 2010-11-10 |
WO2007057790A2 (en) | 2007-05-24 |
CN101312971A (zh) | 2008-11-26 |
HK1126204A1 (en) | 2009-08-28 |
WO2007057790A3 (en) | 2007-10-11 |
ZA200804335B (en) | 2010-05-26 |
MX2008006321A (es) | 2009-03-23 |
EP1957492A2 (en) | 2008-08-20 |
BRPI0618752A2 (pt) | 2011-09-27 |
US8148364B2 (en) | 2012-04-03 |
NZ568014A (en) | 2011-07-29 |
RS51654B (en) | 2011-10-31 |
CY1111125T1 (el) | 2015-06-11 |
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