RU2012133475A - Ингибиторы кинуренин-3-монооксигеназы, фармацевтические композиции и способы их применения - Google Patents
Ингибиторы кинуренин-3-монооксигеназы, фармацевтические композиции и способы их применения Download PDFInfo
- Publication number
- RU2012133475A RU2012133475A RU2012133475/04A RU2012133475A RU2012133475A RU 2012133475 A RU2012133475 A RU 2012133475A RU 2012133475/04 A RU2012133475/04 A RU 2012133475/04A RU 2012133475 A RU2012133475 A RU 2012133475A RU 2012133475 A RU2012133475 A RU 2012133475A
- Authority
- RU
- Russia
- Prior art keywords
- phenyl
- dichloro
- pyrimidine
- chloro
- methyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims 5
- 239000003112 inhibitor Substances 0.000 title 1
- -1 3-chloro-4-trifluoromethoxyphenyl Chemical group 0.000 claims abstract 96
- 150000001875 compounds Chemical class 0.000 claims abstract 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract 16
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims abstract 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract 7
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 7
- 150000002367 halogens Chemical group 0.000 claims abstract 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims abstract 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 3
- 239000000651 prodrug Substances 0.000 claims abstract 3
- 229940002612 prodrug Drugs 0.000 claims abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 150000002431 hydrogen Chemical group 0.000 claims abstract 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
- BIGWXAGEQONZGD-UHFFFAOYSA-N 2h-oxadiazol-5-one Chemical compound O=C1C=NNO1 BIGWXAGEQONZGD-UHFFFAOYSA-N 0.000 claims 10
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 3
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 3
- 159000000000 sodium salts Chemical class 0.000 claims 3
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 claims 3
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 3
- MTOCMLGOPYERKW-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(2h-tetrazol-5-yl)pyrimidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(C=2NN=NN=2)=NC=N1 MTOCMLGOPYERKW-UHFFFAOYSA-N 0.000 claims 2
- SKUQIZNIGNTGFZ-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-6-(2h-tetrazol-5-yl)pyrimidine Chemical compound C1=C(F)C(F)=CC=C1C1=CC(C=2NN=NN=2)=NC=N1 SKUQIZNIGNTGFZ-UHFFFAOYSA-N 0.000 claims 2
- WNENMQUGXZYTTO-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenyl)-6-(2h-tetrazol-5-yl)pyrimidine Chemical compound C1=C(Cl)C(F)=CC=C1C1=CC(C=2NN=NN=2)=NC=N1 WNENMQUGXZYTTO-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 230000000626 neurodegenerative effect Effects 0.000 claims 2
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 2
- 230000007170 pathology Effects 0.000 claims 2
- ROSKCKKWUAUBPC-UHFFFAOYSA-N 2-[6-(3,4-dichlorophenyl)-2-methylpyrimidin-4-yl]-4-methyl-1,3-oxazole Chemical compound CC1=COC(C=2N=C(C)N=C(C=2)C=2C=C(Cl)C(Cl)=CC=2)=N1 ROSKCKKWUAUBPC-UHFFFAOYSA-N 0.000 claims 1
- KGMUYOCFDSQXAE-UHFFFAOYSA-N 2-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-1,3-oxazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(C=2OC=CN=2)=NC=N1 KGMUYOCFDSQXAE-UHFFFAOYSA-N 0.000 claims 1
- UZUWTIHQPXDNIC-UHFFFAOYSA-N 2-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-1,3-thiazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(C=2SC=CN=2)=NC=N1 UZUWTIHQPXDNIC-UHFFFAOYSA-N 0.000 claims 1
- JMGZKBUMZTWCTN-UHFFFAOYSA-N 2-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-1h-benzimidazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(C=2NC3=CC=CC=C3N=2)=NC=N1 JMGZKBUMZTWCTN-UHFFFAOYSA-N 0.000 claims 1
- LNRYOGXIUGDXCK-UHFFFAOYSA-N 2-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-4-methyl-1,3-oxazole Chemical compound CC1=COC(C=2N=CN=C(C=2)C=2C=C(Cl)C(Cl)=CC=2)=N1 LNRYOGXIUGDXCK-UHFFFAOYSA-N 0.000 claims 1
- AFGXONWEIZLGHJ-UHFFFAOYSA-N 2-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-5-methyl-1h-pyrazol-3-one Chemical compound N1C(C)=CC(=O)N1C1=CC(C=2C=C(Cl)C(Cl)=CC=2)=NC=N1 AFGXONWEIZLGHJ-UHFFFAOYSA-N 0.000 claims 1
- WDLSNFQTFQDMLE-UHFFFAOYSA-N 2-[6-(3-chlorophenyl)pyrimidin-4-yl]-1,3-benzoxazole Chemical compound ClC1=CC=CC(C=2N=CN=C(C=2)C=2OC3=CC=CC=C3N=2)=C1 WDLSNFQTFQDMLE-UHFFFAOYSA-N 0.000 claims 1
- DIQUOHCUSXJTGE-UHFFFAOYSA-N 2-[6-(3-chlorophenyl)pyrimidin-4-yl]-1-methylbenzimidazole Chemical compound N=1C2=CC=CC=C2N(C)C=1C(N=CN=1)=CC=1C1=CC=CC(Cl)=C1 DIQUOHCUSXJTGE-UHFFFAOYSA-N 0.000 claims 1
- KDPUXHLJFAMDMJ-UHFFFAOYSA-N 2-[6-(3-chlorophenyl)pyrimidin-4-yl]-1h-benzimidazole Chemical compound ClC1=CC=CC(C=2N=CN=C(C=2)C=2NC3=CC=CC=C3N=2)=C1 KDPUXHLJFAMDMJ-UHFFFAOYSA-N 0.000 claims 1
- HQHXJSFDZSMZLZ-UHFFFAOYSA-N 2-[6-(3-chlorophenyl)pyrimidin-4-yl]-4-methyl-1,3-oxazole Chemical compound CC1=COC(C=2N=CN=C(C=2)C=2C=C(Cl)C=CC=2)=N1 HQHXJSFDZSMZLZ-UHFFFAOYSA-N 0.000 claims 1
- ZAOGPGHFSWAZTM-UHFFFAOYSA-N 2-[6-(3-chlorophenyl)pyrimidin-4-yl]-5,6-difluoro-1h-benzimidazole Chemical compound N1C=2C=C(F)C(F)=CC=2N=C1C(N=CN=1)=CC=1C1=CC=CC(Cl)=C1 ZAOGPGHFSWAZTM-UHFFFAOYSA-N 0.000 claims 1
- JUVYRFJXVZHIFC-UHFFFAOYSA-N 2-[6-(3-chlorophenyl)pyrimidin-4-yl]-6-fluoro-1h-benzimidazole Chemical compound N=1C2=CC(F)=CC=C2NC=1C(N=CN=1)=CC=1C1=CC=CC(Cl)=C1 JUVYRFJXVZHIFC-UHFFFAOYSA-N 0.000 claims 1
- VSHASHJYPUERGY-UHFFFAOYSA-N 3-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-1h-imidazol-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(N2C(NC=C2)=O)=NC=N1 VSHASHJYPUERGY-UHFFFAOYSA-N 0.000 claims 1
- MSYIWJXURWRDKT-UHFFFAOYSA-N 3-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-2h-1,2,4-oxadiazole-5-thione Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(C=2NC(=S)ON=2)=NC=N1 MSYIWJXURWRDKT-UHFFFAOYSA-N 0.000 claims 1
- DJPHEZULAHNZAL-UHFFFAOYSA-N 3-pyrimidin-2-yl-2H-oxadiazole Chemical compound O1NN(C=C1)C1=NC=CC=N1 DJPHEZULAHNZAL-UHFFFAOYSA-N 0.000 claims 1
- ZNKZDGFSYSPQCQ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(1,2,4-triazol-1-yl)pyrimidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(N2N=CN=C2)=NC=N1 ZNKZDGFSYSPQCQ-UHFFFAOYSA-N 0.000 claims 1
- SCAIUCPQLBSMDG-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(1-methyltetrazol-5-yl)pyrimidine Chemical compound CN1N=NN=C1C1=CC(C=2C=C(Cl)C(Cl)=CC=2)=NC=N1 SCAIUCPQLBSMDG-UHFFFAOYSA-N 0.000 claims 1
- JIRSMOUXSFIZTD-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(1h-1,2,4-triazol-5-yl)pyrimidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(C=2NC=NN=2)=NC=N1 JIRSMOUXSFIZTD-UHFFFAOYSA-N 0.000 claims 1
- FCHVNBZJVNRUCR-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(1h-imidazol-2-yl)pyrimidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(C=2NC=CN=2)=NC=N1 FCHVNBZJVNRUCR-UHFFFAOYSA-N 0.000 claims 1
- LNXBAFBGQULGSU-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(1h-pyrazol-5-yl)pyrimidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(C2=NNC=C2)=NC=N1 LNXBAFBGQULGSU-UHFFFAOYSA-N 0.000 claims 1
- IYXFPLVXCRLSKZ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(2-methyltetrazol-5-yl)pyrimidine Chemical compound CN1N=NC(C=2N=CN=C(C=2)C=2C=C(Cl)C(Cl)=CC=2)=N1 IYXFPLVXCRLSKZ-UHFFFAOYSA-N 0.000 claims 1
- ZBHJOTQYFIFNDV-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(4,5-dihydro-1h-imidazol-2-yl)pyrimidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(C=2NCCN=2)=NC=N1 ZBHJOTQYFIFNDV-UHFFFAOYSA-N 0.000 claims 1
- SZAOZTRJZVLXLO-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(5-fluoropyridin-2-yl)pyrimidine Chemical compound N1=CC(F)=CC=C1C1=CC(C=2C=C(Cl)C(Cl)=CC=2)=NC=N1 SZAOZTRJZVLXLO-UHFFFAOYSA-N 0.000 claims 1
- WSFAFIDQMPKXSL-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(5-methyl-1h-1,2,4-triazol-3-yl)pyrimidine Chemical compound N1C(C)=NN=C1C1=CC(C=2C=C(Cl)C(Cl)=CC=2)=NC=N1 WSFAFIDQMPKXSL-UHFFFAOYSA-N 0.000 claims 1
- YMUUSKWZBOGGDX-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-(5-methyl-1h-imidazol-2-yl)pyrimidine Chemical compound CC1=CNC(C=2N=CN=C(C=2)C=2C=C(Cl)C(Cl)=CC=2)=N1 YMUUSKWZBOGGDX-UHFFFAOYSA-N 0.000 claims 1
- PYCPSMXEPSFEJE-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-[3-(trifluoromethyl)pyrazol-1-yl]pyrimidine Chemical compound N1=C(C(F)(F)F)C=CN1C1=CC(C=2C=C(Cl)C(Cl)=CC=2)=NC=N1 PYCPSMXEPSFEJE-UHFFFAOYSA-N 0.000 claims 1
- ALWHQBOIACGJGE-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-[4-(trifluoromethyl)imidazol-1-yl]pyrimidine Chemical compound C1=NC(C(F)(F)F)=CN1C1=CC(C=2C=C(Cl)C(Cl)=CC=2)=NC=N1 ALWHQBOIACGJGE-UHFFFAOYSA-N 0.000 claims 1
- PURBNGDJUSAPDH-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-imidazol-1-ylpyrimidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(N2C=NC=C2)=NC=N1 PURBNGDJUSAPDH-UHFFFAOYSA-N 0.000 claims 1
- QKDPTHAYQCPXSV-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-6-pyrazol-1-ylpyrimidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(N2N=CC=C2)=NC=N1 QKDPTHAYQCPXSV-UHFFFAOYSA-N 0.000 claims 1
- AEWCHHBGHBDHET-UHFFFAOYSA-N 4-(3-chloro-4-propan-2-yloxyphenyl)-6-(2h-tetrazol-5-yl)pyrimidine Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=CC(C=2NN=NN=2)=NC=N1 AEWCHHBGHBDHET-UHFFFAOYSA-N 0.000 claims 1
- UGYNJZXCCMRSAY-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-(1,2,4-triazol-1-yl)pyrimidine Chemical compound ClC1=CC=CC(C=2N=CN=C(C=2)N2N=CN=C2)=C1 UGYNJZXCCMRSAY-UHFFFAOYSA-N 0.000 claims 1
- WWGQYSXKRDZEQL-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-(1-methyltetrazol-5-yl)pyrimidine Chemical compound CN1N=NN=C1C1=CC(C=2C=C(Cl)C=CC=2)=NC=N1 WWGQYSXKRDZEQL-UHFFFAOYSA-N 0.000 claims 1
- LGGGIVRSZVEHDF-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-(1h-1,2,4-triazol-5-yl)pyrimidine Chemical compound ClC1=CC=CC(C=2N=CN=C(C=2)C=2NC=NN=2)=C1 LGGGIVRSZVEHDF-UHFFFAOYSA-N 0.000 claims 1
- LRAVNVHTOASBPS-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-(2-methyltetrazol-5-yl)pyrimidine Chemical compound CN1N=NC(C=2N=CN=C(C=2)C=2C=C(Cl)C=CC=2)=N1 LRAVNVHTOASBPS-UHFFFAOYSA-N 0.000 claims 1
- KRYPSLGAMUHGTE-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-(2h-tetrazol-5-yl)pyrimidine Chemical compound ClC1=CC=CC(C=2N=CN=C(C=2)C=2NN=NN=2)=C1 KRYPSLGAMUHGTE-UHFFFAOYSA-N 0.000 claims 1
- NZHPCOKTLUVIDD-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-(tetrazol-1-yl)pyrimidine Chemical compound ClC1=CC=CC(C=2N=CN=C(C=2)N2N=NN=C2)=C1 NZHPCOKTLUVIDD-UHFFFAOYSA-N 0.000 claims 1
- DAROHEOKVSJSFA-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-imidazol-1-ylpyrimidine Chemical compound ClC1=CC=CC(C=2N=CN=C(C=2)N2C=NC=C2)=C1 DAROHEOKVSJSFA-UHFFFAOYSA-N 0.000 claims 1
- BXHOWMJGICQXHF-UHFFFAOYSA-N 4-(3-chlorophenyl)-6-pyrazol-1-ylpyrimidine Chemical compound ClC1=CC=CC(C=2N=CN=C(C=2)N2N=CC=C2)=C1 BXHOWMJGICQXHF-UHFFFAOYSA-N 0.000 claims 1
- PFZSBRMSYRLMCE-UHFFFAOYSA-N 4-(3-fluoro-4-methylphenyl)-6-(2h-tetrazol-5-yl)pyrimidine Chemical compound C1=C(F)C(C)=CC=C1C1=CC(C=2NN=NN=2)=NC=N1 PFZSBRMSYRLMCE-UHFFFAOYSA-N 0.000 claims 1
- BQTLWRJCOSPNDU-UHFFFAOYSA-N 4-[3-chloro-4-(trifluoromethoxy)phenyl]-6-(2h-tetrazol-5-yl)pyrimidine Chemical compound C1=C(Cl)C(OC(F)(F)F)=CC=C1C1=CC(C=2NN=NN=2)=NC=N1 BQTLWRJCOSPNDU-UHFFFAOYSA-N 0.000 claims 1
- PFIWBAMCCSFJFE-UHFFFAOYSA-N 4-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-1,2-dimethylpyrazol-3-one Chemical compound O=C1N(C)N(C)C=C1C1=CC(C=2C=C(Cl)C(Cl)=CC=2)=NC=N1 PFIWBAMCCSFJFE-UHFFFAOYSA-N 0.000 claims 1
- SBPMGWKYHYKRLR-UHFFFAOYSA-N 4-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-1,3-dihydroimidazol-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(C=2NC(=O)NC=2)=NC=N1 SBPMGWKYHYKRLR-UHFFFAOYSA-N 0.000 claims 1
- LMJHXFQNUUCRNJ-UHFFFAOYSA-N 4-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-2-methyl-1h-pyrazol-3-one Chemical compound O=C1N(C)NC=C1C1=CC(C=2C=C(Cl)C(Cl)=CC=2)=NC=N1 LMJHXFQNUUCRNJ-UHFFFAOYSA-N 0.000 claims 1
- OLDJDFWTWFAWRM-UHFFFAOYSA-N 4-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]piperazin-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(N2CC(=O)NCC2)=NC=N1 OLDJDFWTWFAWRM-UHFFFAOYSA-N 0.000 claims 1
- MVLZWTSKQRHYQE-UHFFFAOYSA-N 4-[6-(3,5-dichlorophenyl)pyrimidin-4-yl]piperazin-2-one Chemical compound ClC1=CC(Cl)=CC(C=2N=CN=C(C=2)N2CC(=O)NCC2)=C1 MVLZWTSKQRHYQE-UHFFFAOYSA-N 0.000 claims 1
- KIAQGYDLRQLECF-UHFFFAOYSA-N 5-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-1,2-dihydro-1,2,4-triazol-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC(C=2NC(=O)NN=2)=NC=N1 KIAQGYDLRQLECF-UHFFFAOYSA-N 0.000 claims 1
- PPMMGNWVXQVXGT-UHFFFAOYSA-N 6-[6-(3,4-dichlorophenyl)pyrimidin-4-yl]-n-methylpyridine-3-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1C1=CC(C=2C=C(Cl)C(Cl)=CC=2)=NC=N1 PPMMGNWVXQVXGT-UHFFFAOYSA-N 0.000 claims 1
- BHSBPFTWYYSYDZ-UHFFFAOYSA-N 6-chloro-2-[6-(3-chlorophenyl)pyrimidin-4-yl]-1h-benzimidazole Chemical compound ClC1=CC=CC(C=2N=CN=C(C=2)C=2NC3=CC(Cl)=CC=C3N=2)=C1 BHSBPFTWYYSYDZ-UHFFFAOYSA-N 0.000 claims 1
- 208000002381 Brain Hypoxia Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 206010059150 Cerebrosclerosis Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims 1
- 208000001089 Multiple system atrophy Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 201000004810 Vascular dementia Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 208000031237 olivopontocerebellar atrophy Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 210000000278 spinal cord Anatomy 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
Classifications
-
- 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
-
- 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
- C07D239/30—Halogen atoms or nitro radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
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-
2011
- 2011-01-20 AU AU2011207229A patent/AU2011207229B2/en not_active Expired - Fee Related
- 2011-01-20 BR BR112012018500A patent/BR112012018500A2/pt not_active IP Right Cessation
- 2011-01-20 CA CA2787365A patent/CA2787365A1/en not_active Abandoned
- 2011-01-20 RU RU2012133475/04A patent/RU2012133475A/ru not_active Application Discontinuation
- 2011-01-20 EP EP11735184.1A patent/EP2528441A4/en not_active Withdrawn
- 2011-01-20 US US13/575,019 patent/US8883785B2/en active Active
- 2011-01-20 NZ NZ601547A patent/NZ601547A/en not_active IP Right Cessation
- 2011-01-20 WO PCT/US2011/021890 patent/WO2011091153A1/en not_active Ceased
- 2011-01-20 MX MX2012008346A patent/MX2012008346A/es not_active Application Discontinuation
- 2011-01-20 PH PH1/2012/501480A patent/PH12012501480A1/en unknown
- 2011-01-20 CN CN201180015784.XA patent/CN102811620B/zh not_active Expired - Fee Related
- 2011-01-20 KR KR1020127021570A patent/KR20120131161A/ko not_active Withdrawn
- 2011-01-20 JP JP2012550116A patent/JP2013518046A/ja active Pending
- 2011-01-20 SG SG2012052189A patent/SG182534A1/en unknown
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2012
- 2012-08-17 ZA ZA2012/06223A patent/ZA201206223B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2011207229A1 (en) | 2012-08-16 |
| KR20120131161A (ko) | 2012-12-04 |
| WO2011091153A1 (en) | 2011-07-28 |
| US8883785B2 (en) | 2014-11-11 |
| CN102811620B (zh) | 2015-03-25 |
| NZ601547A (en) | 2014-04-30 |
| US20130029988A1 (en) | 2013-01-31 |
| MX2012008346A (es) | 2012-11-12 |
| BR112012018500A2 (pt) | 2016-08-16 |
| PH12012501480A1 (en) | 2012-10-22 |
| ZA201206223B (en) | 2013-04-24 |
| SG182534A1 (en) | 2012-08-30 |
| JP2013518046A (ja) | 2013-05-20 |
| AU2011207229B2 (en) | 2015-02-12 |
| CN102811620A (zh) | 2012-12-05 |
| CA2787365A1 (en) | 2011-07-28 |
| EP2528441A1 (en) | 2012-12-05 |
| EP2528441A4 (en) | 2013-07-10 |
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