HRP20161495T1 - Novi derivati pirimidina kao inhibitori fosfodiesteraze 10 (pde-10) - Google Patents
Novi derivati pirimidina kao inhibitori fosfodiesteraze 10 (pde-10) Download PDFInfo
- Publication number
- HRP20161495T1 HRP20161495T1 HRP20161495TT HRP20161495T HRP20161495T1 HR P20161495 T1 HRP20161495 T1 HR P20161495T1 HR P20161495T T HRP20161495T T HR P20161495TT HR P20161495 T HRP20161495 T HR P20161495T HR P20161495 T1 HRP20161495 T1 HR P20161495T1
- Authority
- HR
- Croatia
- Prior art keywords
- bromo
- diamine
- pyrimidin
- group
- pyrazol
- Prior art date
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- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title claims 3
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 title claims 3
- 239000003112 inhibitor Substances 0.000 title 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 3
- 230000001575 pathological effect Effects 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- VHIFCIWHFZTPJG-UHFFFAOYSA-N 1-[4-amino-5-bromo-6-(2-methoxyethylamino)pyrimidin-2-yl]pyrazole-4-carboxylic acid Chemical compound NC1=C(Br)C(NCCOC)=NC(N2N=CC(=C2)C(O)=O)=N1 VHIFCIWHFZTPJG-UHFFFAOYSA-N 0.000 claims 1
- SBKZEROFGFUCDC-UHFFFAOYSA-N 1-[4-amino-5-bromo-6-(cyclopropylmethylamino)pyrimidin-2-yl]pyrazole-4-carboxylic acid Chemical compound BrC=1C(N)=NC(N2N=CC(=C2)C(O)=O)=NC=1NCC1CC1 SBKZEROFGFUCDC-UHFFFAOYSA-N 0.000 claims 1
- TXLMUZCLPXERKW-UHFFFAOYSA-N 1-[4-amino-5-bromo-6-(ethylamino)pyrimidin-2-yl]pyrazole-4-carboxylic acid Chemical compound NC1=C(Br)C(NCC)=NC(N2N=CC(=C2)C(O)=O)=N1 TXLMUZCLPXERKW-UHFFFAOYSA-N 0.000 claims 1
- NYHMAQKRJSKMLL-UHFFFAOYSA-N 1-[4-amino-5-bromo-6-(prop-2-ynylamino)pyrimidin-2-yl]pyrazole-4-carboxylic acid Chemical compound C#CCNC1=C(Br)C(N)=NC(N2N=CC(=C2)C(O)=O)=N1 NYHMAQKRJSKMLL-UHFFFAOYSA-N 0.000 claims 1
- CLOWJUNQSSLMHT-UHFFFAOYSA-N 1-[4-amino-5-bromo-6-(propan-2-ylamino)pyrimidin-2-yl]pyrazole-4-carboxylic acid Chemical compound NC1=C(Br)C(NC(C)C)=NC(N2N=CC(=C2)C(O)=O)=N1 CLOWJUNQSSLMHT-UHFFFAOYSA-N 0.000 claims 1
- XSHKEOPRVNFWMZ-UHFFFAOYSA-N 1-[4-amino-5-bromo-6-[(4-methyl-1,3-thiazol-5-yl)methylamino]pyrimidin-2-yl]pyrazole-4-carboxylic acid Chemical compound N1=CSC(CNC=2C(=C(N)N=C(N=2)N2N=CC(=C2)C(O)=O)Br)=C1C XSHKEOPRVNFWMZ-UHFFFAOYSA-N 0.000 claims 1
- WGGWEGPYXZHMLB-UHFFFAOYSA-N 4-n-(1h-benzimidazol-2-ylmethyl)-5-bromo-2-indazol-1-yl-6-n-prop-2-ynylpyrimidine-4,6-diamine Chemical compound N1=CC2=CC=CC=C2N1C1=NC(NCC#C)=C(Br)C(NCC=2NC3=CC=CC=C3N=2)=N1 WGGWEGPYXZHMLB-UHFFFAOYSA-N 0.000 claims 1
- XPNCUCCYJSMTNQ-UHFFFAOYSA-N 4-n-(1h-benzimidazol-2-ylmethyl)-5-bromo-2-indazol-1-ylpyrimidine-4,6-diamine Chemical compound N1=CC2=CC=CC=C2N1C1=NC(NCC=2NC3=CC=CC=C3N=2)=C(Br)C(N)=N1 XPNCUCCYJSMTNQ-UHFFFAOYSA-N 0.000 claims 1
- ABUSXELVCQKIJQ-UHFFFAOYSA-N 4-n-(1h-benzimidazol-2-ylmethyl)-5-bromo-2-pyrazol-1-ylpyrimidine-4,6-diamine Chemical compound N=1C(NCC=2NC3=CC=CC=C3N=2)=C(Br)C(N)=NC=1N1C=CC=N1 ABUSXELVCQKIJQ-UHFFFAOYSA-N 0.000 claims 1
- IGUPBCSERVLCJN-UHFFFAOYSA-N 4-n-(1h-benzimidazol-2-ylmethyl)-5-bromo-6-n-ethyl-2-(4-pyrimidin-4-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound N=1C(NCC=2NC3=CC=CC=C3N=2)=C(Br)C(NCC)=NC=1N(N=C1)C=C1C1=CC=NC=N1 IGUPBCSERVLCJN-UHFFFAOYSA-N 0.000 claims 1
- QQXOFYBKABLFFP-UHFFFAOYSA-N 4-n-(1h-benzimidazol-2-ylmethyl)-5-bromo-6-n-prop-2-ynyl-2-(4-pyridin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound N1=C(NCC=2NC3=CC=CC=C3N=2)C(Br)=C(NCC#C)N=C1N(N=C1)C=C1C1=CC=CC=N1 QQXOFYBKABLFFP-UHFFFAOYSA-N 0.000 claims 1
- QYJQVKOFFIENGF-UHFFFAOYSA-N 5-bromo-2-(4-pyridin-2-ylpyrazol-1-yl)-4-n-(1,3-thiazol-5-ylmethyl)pyrimidine-4,6-diamine Chemical compound BrC=1C(N)=NC(N2N=CC(=C2)C=2N=CC=CC=2)=NC=1NCC1=CN=CS1 QYJQVKOFFIENGF-UHFFFAOYSA-N 0.000 claims 1
- FJARMMODQHZNPB-UHFFFAOYSA-N 5-bromo-2-(4-pyridin-4-ylpyrazol-1-yl)-4-n-(1,3-thiazol-5-ylmethyl)pyrimidine-4,6-diamine Chemical compound BrC=1C(N)=NC(N2N=CC(=C2)C=2C=CN=CC=2)=NC=1NCC1=CN=CS1 FJARMMODQHZNPB-UHFFFAOYSA-N 0.000 claims 1
- ZZEHHBSJEUWREP-UHFFFAOYSA-N 5-bromo-2-[4-(4-chlorophenyl)pyrazol-1-yl]-4-n-ethylpyrimidine-4,6-diamine Chemical compound NC1=C(Br)C(NCC)=NC(N2N=CC(=C2)C=2C=CC(Cl)=CC=2)=N1 ZZEHHBSJEUWREP-UHFFFAOYSA-N 0.000 claims 1
- AHHPJTRYYMNSIA-UHFFFAOYSA-N 5-bromo-2-[4-(4-chlorophenyl)pyrazol-1-yl]-4-n-prop-2-ynylpyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(N)=NC(N2N=CC(=C2)C=2C=CC(Cl)=CC=2)=N1 AHHPJTRYYMNSIA-UHFFFAOYSA-N 0.000 claims 1
- YUWMSAPDGLGOKO-UHFFFAOYSA-N 5-bromo-2-indazol-1-yl-4-n-(1,3-thiazol-5-ylmethyl)pyrimidine-4,6-diamine Chemical compound BrC=1C(N)=NC(N2C3=CC=CC=C3C=N2)=NC=1NCC1=CN=CS1 YUWMSAPDGLGOKO-UHFFFAOYSA-N 0.000 claims 1
- AGZVUBIPUFBNIQ-UHFFFAOYSA-N 5-bromo-2-indazol-1-yl-4-n-(2-methoxyethyl)pyrimidine-4,6-diamine Chemical compound NC1=C(Br)C(NCCOC)=NC(N2C3=CC=CC=C3C=N2)=N1 AGZVUBIPUFBNIQ-UHFFFAOYSA-N 0.000 claims 1
- ADVTUDKXHRVXNC-UHFFFAOYSA-N 5-bromo-2-indazol-1-yl-4-n-(oxan-4-yl)-6-n-prop-2-ynylpyrimidine-4,6-diamine Chemical compound BrC1=C(NCC#C)N=C(N2C3=CC=CC=C3C=N2)N=C1NC1CCOCC1 ADVTUDKXHRVXNC-UHFFFAOYSA-N 0.000 claims 1
- PXOKRGLRJOJXLP-UHFFFAOYSA-N 5-bromo-2-indazol-1-yl-4-n-(oxan-4-yl)pyrimidine-4,6-diamine Chemical compound BrC=1C(N)=NC(N2C3=CC=CC=C3C=N2)=NC=1NC1CCOCC1 PXOKRGLRJOJXLP-UHFFFAOYSA-N 0.000 claims 1
- SGKPBPSTVILYGB-UHFFFAOYSA-N 5-bromo-2-indazol-1-yl-4-n-[(1-methylpyrazol-4-yl)methyl]pyrimidine-4,6-diamine Chemical compound C1=NN(C)C=C1CNC1=NC(N2C3=CC=CC=C3C=N2)=NC(N)=C1Br SGKPBPSTVILYGB-UHFFFAOYSA-N 0.000 claims 1
- XNPFGZDYCMIIFM-UHFFFAOYSA-N 5-bromo-2-indazol-1-yl-4-n-[(2-methyl-1,3-thiazol-4-yl)methyl]pyrimidine-4,6-diamine Chemical compound S1C(C)=NC(CNC=2C(=C(N)N=C(N=2)N2C3=CC=CC=C3C=N2)Br)=C1 XNPFGZDYCMIIFM-UHFFFAOYSA-N 0.000 claims 1
- DGFHPCHDAOKRIG-UHFFFAOYSA-N 5-bromo-2-indazol-1-yl-4-n-[(4-methyl-1,3-thiazol-5-yl)methyl]pyrimidine-4,6-diamine Chemical compound N1=CSC(CNC=2C(=C(N)N=C(N=2)N2C3=CC=CC=C3C=N2)Br)=C1C DGFHPCHDAOKRIG-UHFFFAOYSA-N 0.000 claims 1
- HOEWDHDEZCYQPM-UHFFFAOYSA-N 5-bromo-2-indazol-1-yl-4-n-prop-2-ynylpyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(N)=NC(N2C3=CC=CC=C3C=N2)=N1 HOEWDHDEZCYQPM-UHFFFAOYSA-N 0.000 claims 1
- SXGWEVBRPAHFEC-UHFFFAOYSA-N 5-bromo-2-indazol-1-yl-6-pyrazol-1-ylpyrimidin-4-amine Chemical compound BrC=1C(N)=NC(N2C3=CC=CC=C3C=N2)=NC=1N1C=CC=N1 SXGWEVBRPAHFEC-UHFFFAOYSA-N 0.000 claims 1
- JGLSQVKAGHSSJI-UHFFFAOYSA-N 5-bromo-2-pyrazolo[3,4-c]pyridin-1-yl-4-n-(1,3-thiazol-5-ylmethyl)pyrimidine-4,6-diamine Chemical compound BrC=1C(N)=NC(N2C3=CN=CC=C3C=N2)=NC=1NCC1=CN=CS1 JGLSQVKAGHSSJI-UHFFFAOYSA-N 0.000 claims 1
- LPNOHJNNLYLBPM-UHFFFAOYSA-N 5-bromo-4-n-(1,3-thiazol-5-ylmethyl)-2-(1,2,4-triazol-1-yl)pyrimidine-4,6-diamine Chemical compound BrC=1C(N)=NC(N2N=CN=C2)=NC=1NCC1=CN=CS1 LPNOHJNNLYLBPM-UHFFFAOYSA-N 0.000 claims 1
- RWWDDVOZZAKQCD-UHFFFAOYSA-N 5-bromo-4-n-(2-methoxyethyl)-2-(1,2,4-triazol-1-yl)pyrimidine-4,6-diamine Chemical compound NC1=C(Br)C(NCCOC)=NC(N2N=CN=C2)=N1 RWWDDVOZZAKQCD-UHFFFAOYSA-N 0.000 claims 1
- UTVZWWLUVWFWHR-UHFFFAOYSA-N 5-bromo-4-n-(2-methoxyethyl)-2-(4-pyridin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound NC1=C(Br)C(NCCOC)=NC(N2N=CC(=C2)C=2N=CC=CC=2)=N1 UTVZWWLUVWFWHR-UHFFFAOYSA-N 0.000 claims 1
- GZWLUYJHWNOOKB-UHFFFAOYSA-N 5-bromo-4-n-(2-methoxyethyl)-2-pyrazol-1-ylpyrimidine-4,6-diamine Chemical compound NC1=C(Br)C(NCCOC)=NC(N2N=CC=C2)=N1 GZWLUYJHWNOOKB-UHFFFAOYSA-N 0.000 claims 1
- FVQNFPYNALLXNX-UHFFFAOYSA-N 5-bromo-4-n-(2-methoxyethyl)-2-pyrazolo[3,4-c]pyridin-1-ylpyrimidine-4,6-diamine Chemical compound NC1=C(Br)C(NCCOC)=NC(N2C3=CN=CC=C3C=N2)=N1 FVQNFPYNALLXNX-UHFFFAOYSA-N 0.000 claims 1
- LMDFJLOJQVLTDO-UHFFFAOYSA-N 5-bromo-4-n-(cyclopropylmethyl)-2-(1,2,4-triazol-1-yl)pyrimidine-4,6-diamine Chemical compound BrC=1C(N)=NC(N2N=CN=C2)=NC=1NCC1CC1 LMDFJLOJQVLTDO-UHFFFAOYSA-N 0.000 claims 1
- NEWLRXGDUSSRMD-UHFFFAOYSA-N 5-bromo-4-n-(cyclopropylmethyl)-2-(4-pyridin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound BrC=1C(N)=NC(N2N=CC(=C2)C=2N=CC=CC=2)=NC=1NCC1CC1 NEWLRXGDUSSRMD-UHFFFAOYSA-N 0.000 claims 1
- UVXKPTAMFWNRRI-UHFFFAOYSA-N 5-bromo-4-n-(cyclopropylmethyl)-2-indazol-1-yl-6-n-prop-2-ynylpyrimidine-4,6-diamine Chemical compound BrC1=C(NCC#C)N=C(N2C3=CC=CC=C3C=N2)N=C1NCC1CC1 UVXKPTAMFWNRRI-UHFFFAOYSA-N 0.000 claims 1
- OFWOOSRVYJIHGB-UHFFFAOYSA-N 5-bromo-4-n-(cyclopropylmethyl)-2-indazol-1-ylpyrimidine-4,6-diamine Chemical compound BrC=1C(N)=NC(N2C3=CC=CC=C3C=N2)=NC=1NCC1CC1 OFWOOSRVYJIHGB-UHFFFAOYSA-N 0.000 claims 1
- YOUQGLAXDFCVOM-UHFFFAOYSA-N 5-bromo-4-n-(cyclopropylmethyl)-2-pyrazolo[3,4-c]pyridin-1-ylpyrimidine-4,6-diamine Chemical compound BrC=1C(N)=NC(N2C3=CN=CC=C3C=N2)=NC=1NCC1CC1 YOUQGLAXDFCVOM-UHFFFAOYSA-N 0.000 claims 1
- AWJLKKHXUYYCQU-UHFFFAOYSA-N 5-bromo-4-n-(cyclopropylmethyl)-6-n-ethyl-2-(4-pyrimidin-4-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound BrC=1C(NCC)=NC(N2N=CC(=C2)C=2N=CN=CC=2)=NC=1NCC1CC1 AWJLKKHXUYYCQU-UHFFFAOYSA-N 0.000 claims 1
- MYQITIOJRRCQEA-UHFFFAOYSA-N 5-bromo-4-n-(cyclopropylmethyl)-6-n-prop-2-ynyl-2-(4-pyridin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound BrC1=C(NCC#C)N=C(N2N=CC(=C2)C=2N=CC=CC=2)N=C1NCC1CC1 MYQITIOJRRCQEA-UHFFFAOYSA-N 0.000 claims 1
- BWSWSIOGMRKWAU-UHFFFAOYSA-N 5-bromo-4-n-(oxan-4-yl)-2-(4-quinolin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound BrC=1C(N)=NC(N2N=CC(=C2)C=2N=C3C=CC=CC3=CC=2)=NC=1NC1CCOCC1 BWSWSIOGMRKWAU-UHFFFAOYSA-N 0.000 claims 1
- JVFABXMLUPXVBG-UHFFFAOYSA-N 5-bromo-4-n-(oxan-4-yl)-6-n-prop-2-ynyl-2-(4-pyridin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound BrC1=C(NCC#C)N=C(N2N=CC(=C2)C=2N=CC=CC=2)N=C1NC1CCOCC1 JVFABXMLUPXVBG-UHFFFAOYSA-N 0.000 claims 1
- AJHLVMIANNAUSS-UHFFFAOYSA-N 5-bromo-4-n-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-(4-quinolin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound S1C(C)=NC(CNC=2C(=C(N)N=C(N=2)N2N=CC(=C2)C=2N=C3C=CC=CC3=CC=2)Br)=C1 AJHLVMIANNAUSS-UHFFFAOYSA-N 0.000 claims 1
- IJWBLJOTLBMDDI-UHFFFAOYSA-N 5-bromo-4-n-[(4-methyl-1,3-thiazol-5-yl)methyl]-2-(1,2,4-triazol-1-yl)pyrimidine-4,6-diamine Chemical compound N1=CSC(CNC=2C(=C(N)N=C(N=2)N2N=CN=C2)Br)=C1C IJWBLJOTLBMDDI-UHFFFAOYSA-N 0.000 claims 1
- LIVRZEMVHNFQCE-UHFFFAOYSA-N 5-bromo-4-n-[(4-methyl-1,3-thiazol-5-yl)methyl]-2-(4-pyrazin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound N1=CSC(CNC=2C(=C(N)N=C(N=2)N2N=CC(=C2)C=2N=CC=NC=2)Br)=C1C LIVRZEMVHNFQCE-UHFFFAOYSA-N 0.000 claims 1
- SPUGAJRTEPSGNK-UHFFFAOYSA-N 5-bromo-4-n-[(4-methyl-1,3-thiazol-5-yl)methyl]-2-(4-pyridin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound N1=CSC(CNC=2C(=C(N)N=C(N=2)N2N=CC(=C2)C=2N=CC=CC=2)Br)=C1C SPUGAJRTEPSGNK-UHFFFAOYSA-N 0.000 claims 1
- JNLBMGZUUBFSFY-UHFFFAOYSA-N 5-bromo-4-n-[(4-methyl-1,3-thiazol-5-yl)methyl]-2-(4-quinolin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound N1=CSC(CNC=2C(=C(N)N=C(N=2)N2N=CC(=C2)C=2N=C3C=CC=CC3=CC=2)Br)=C1C JNLBMGZUUBFSFY-UHFFFAOYSA-N 0.000 claims 1
- IVDHYWONEWAJCC-UHFFFAOYSA-N 5-bromo-4-n-[(4-methyl-1,3-thiazol-5-yl)methyl]-2-pyrazol-1-ylpyrimidine-4,6-diamine Chemical compound N1=CSC(CNC=2C(=C(N)N=C(N=2)N2N=CC=C2)Br)=C1C IVDHYWONEWAJCC-UHFFFAOYSA-N 0.000 claims 1
- FMHPVRJBVKEXCW-UHFFFAOYSA-N 5-bromo-4-n-[(4-methyl-1,3-thiazol-5-yl)methyl]-2-pyrazolo[3,4-b]pyridin-1-ylpyrimidine-4,6-diamine Chemical compound N1=CSC(CNC=2C(=C(N)N=C(N=2)N2C3=NC=CC=C3C=N2)Br)=C1C FMHPVRJBVKEXCW-UHFFFAOYSA-N 0.000 claims 1
- HOAHNWHRWZOBLC-UHFFFAOYSA-N 5-bromo-4-n-[(4-methyl-1,3-thiazol-5-yl)methyl]-2-pyrazolo[3,4-c]pyridin-1-ylpyrimidine-4,6-diamine Chemical compound N1=CSC(CNC=2C(=C(N)N=C(N=2)N2C3=CN=CC=C3C=N2)Br)=C1C HOAHNWHRWZOBLC-UHFFFAOYSA-N 0.000 claims 1
- VGIKUPLYZUBYQM-UHFFFAOYSA-N 5-bromo-4-n-[(4-methyl-1,3-thiazol-5-yl)methyl]-2-pyrazolo[4,3-b]pyridin-1-ylpyrimidine-4,6-diamine Chemical compound N1=CSC(CNC=2C(=C(N)N=C(N=2)N2C3=CC=CN=C3C=N2)Br)=C1C VGIKUPLYZUBYQM-UHFFFAOYSA-N 0.000 claims 1
- MWJTXJDTDLLMCG-UHFFFAOYSA-N 5-bromo-4-n-[(4-methyl-1,3-thiazol-5-yl)methyl]-2-pyrazolo[4,3-c]pyridin-1-ylpyrimidine-4,6-diamine Chemical compound N1=CSC(CNC=2C(=C(N)N=C(N=2)N2C3=CC=NC=C3C=N2)Br)=C1C MWJTXJDTDLLMCG-UHFFFAOYSA-N 0.000 claims 1
- XYQXDGPUAUBHLH-UHFFFAOYSA-N 5-bromo-4-n-ethyl-2-(4-phenylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound NC1=C(Br)C(NCC)=NC(N2N=CC(=C2)C=2C=CC=CC=2)=N1 XYQXDGPUAUBHLH-UHFFFAOYSA-N 0.000 claims 1
- UPLHPTCBVIHGDZ-UHFFFAOYSA-N 5-bromo-4-n-ethyl-2-(4-pyridin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound NC1=C(Br)C(NCC)=NC(N2N=CC(=C2)C=2N=CC=CC=2)=N1 UPLHPTCBVIHGDZ-UHFFFAOYSA-N 0.000 claims 1
- WNKRPOMIFBYNBG-UHFFFAOYSA-N 5-bromo-4-n-ethyl-2-(4-pyrimidin-4-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound NC1=C(Br)C(NCC)=NC(N2N=CC(=C2)C=2N=CN=CC=2)=N1 WNKRPOMIFBYNBG-UHFFFAOYSA-N 0.000 claims 1
- FNPPJDANMAXVBF-UHFFFAOYSA-N 5-bromo-4-n-ethyl-2-(4-quinolin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound NC1=C(Br)C(NCC)=NC(N2N=CC(=C2)C=2N=C3C=CC=CC3=CC=2)=N1 FNPPJDANMAXVBF-UHFFFAOYSA-N 0.000 claims 1
- VRQWKQRCPAKJKB-UHFFFAOYSA-N 5-bromo-4-n-ethyl-2-indazol-1-ylpyrimidine-4,6-diamine Chemical compound NC1=C(Br)C(NCC)=NC(N2C3=CC=CC=C3C=N2)=N1 VRQWKQRCPAKJKB-UHFFFAOYSA-N 0.000 claims 1
- OQCWNHHZPYJHQR-UHFFFAOYSA-N 5-bromo-4-n-prop-2-ynyl-2-(1,2,4-triazol-1-yl)pyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(N)=NC(N2N=CN=C2)=N1 OQCWNHHZPYJHQR-UHFFFAOYSA-N 0.000 claims 1
- ZDIICMSESCMMEY-UHFFFAOYSA-N 5-bromo-4-n-prop-2-ynyl-2-(4-pyrazin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(N)=NC(N2N=CC(=C2)C=2N=CC=NC=2)=N1 ZDIICMSESCMMEY-UHFFFAOYSA-N 0.000 claims 1
- AILVOCMYPOOJFN-UHFFFAOYSA-N 5-bromo-4-n-prop-2-ynyl-2-(4-pyridin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(N)=NC(N2N=CC(=C2)C=2N=CC=CC=2)=N1 AILVOCMYPOOJFN-UHFFFAOYSA-N 0.000 claims 1
- HBSVGQZZUPCQPI-UHFFFAOYSA-N 5-bromo-4-n-prop-2-ynyl-2-(4-pyridin-4-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(N)=NC(N2N=CC(=C2)C=2C=CN=CC=2)=N1 HBSVGQZZUPCQPI-UHFFFAOYSA-N 0.000 claims 1
- YGVMDAQTMFZIHL-UHFFFAOYSA-N 5-bromo-4-n-prop-2-ynyl-2-(4-quinolin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(N)=NC(N2N=CC(=C2)C=2N=C3C=CC=CC3=CC=2)=N1 YGVMDAQTMFZIHL-UHFFFAOYSA-N 0.000 claims 1
- VQEVRBXZYGZYEI-UHFFFAOYSA-N 5-bromo-4-n-prop-2-ynyl-2-pyrazolo[3,4-b]pyridin-1-ylpyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(N)=NC(N2C3=NC=CC=C3C=N2)=N1 VQEVRBXZYGZYEI-UHFFFAOYSA-N 0.000 claims 1
- YHTZSINAEGGMBT-UHFFFAOYSA-N 5-bromo-4-n-prop-2-ynyl-2-pyrazolo[3,4-c]pyridin-1-ylpyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(N)=NC(N2C3=CN=CC=C3C=N2)=N1 YHTZSINAEGGMBT-UHFFFAOYSA-N 0.000 claims 1
- VVGIKVHMXDLTCW-UHFFFAOYSA-N 5-bromo-4-n-prop-2-ynyl-2-pyrazolo[4,3-b]pyridin-1-ylpyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(N)=NC(N2C3=CC=CN=C3C=N2)=N1 VVGIKVHMXDLTCW-UHFFFAOYSA-N 0.000 claims 1
- UGXCNYLVCURQDN-UHFFFAOYSA-N 5-bromo-4-n-prop-2-ynyl-2-pyrazolo[4,3-c]pyridin-1-ylpyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(N)=NC(N2C3=CC=NC=C3C=N2)=N1 UGXCNYLVCURQDN-UHFFFAOYSA-N 0.000 claims 1
- ZNQNZXVPHBQGBE-UHFFFAOYSA-N 5-bromo-6-n-ethyl-2-indazol-1-yl-4-n-prop-2-ynylpyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(NCC)=NC(N2C3=CC=CC=C3C=N2)=N1 ZNQNZXVPHBQGBE-UHFFFAOYSA-N 0.000 claims 1
- QLYBACHYAAJHBI-UHFFFAOYSA-N 5-bromo-6-n-ethyl-4-n-(oxan-4-yl)-2-(4-pyrimidin-4-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound BrC=1C(NCC)=NC(N2N=CC(=C2)C=2N=CN=CC=2)=NC=1NC1CCOCC1 QLYBACHYAAJHBI-UHFFFAOYSA-N 0.000 claims 1
- ZDJQBTJLWVVNBV-UHFFFAOYSA-N 5-bromo-6-n-ethyl-4-n-prop-2-ynyl-2-(4-pyridin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(NCC)=NC(N2N=CC(=C2)C=2N=CC=CC=2)=N1 ZDJQBTJLWVVNBV-UHFFFAOYSA-N 0.000 claims 1
- PAVMFAHQYHDVSC-UHFFFAOYSA-N 5-bromo-6-n-ethyl-4-n-prop-2-ynyl-2-(4-pyrimidin-4-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound C#CCNC1=C(Br)C(NCC)=NC(N2N=CC(=C2)C=2N=CN=CC=2)=N1 PAVMFAHQYHDVSC-UHFFFAOYSA-N 0.000 claims 1
- KBSWVSAKXKGNRS-UHFFFAOYSA-N 5-bromo-6-pyrazol-1-yl-2-(1,2,4-triazol-1-yl)pyrimidin-4-amine Chemical compound BrC=1C(N)=NC(N2N=CN=C2)=NC=1N1C=CC=N1 KBSWVSAKXKGNRS-UHFFFAOYSA-N 0.000 claims 1
- YDJHMBNHVDULSX-UHFFFAOYSA-N 5-bromo-6-pyrazol-1-yl-2-(4-pyridin-2-ylpyrazol-1-yl)pyrimidin-4-amine Chemical compound BrC=1C(N)=NC(N2N=CC(=C2)C=2N=CC=CC=2)=NC=1N1C=CC=N1 YDJHMBNHVDULSX-UHFFFAOYSA-N 0.000 claims 1
- MRBXWMSDNYIENV-UHFFFAOYSA-N 5-bromo-6-pyrazol-1-yl-2-(4-pyridin-4-ylpyrazol-1-yl)pyrimidin-4-amine Chemical compound BrC=1C(N)=NC(N2N=CC(=C2)C=2C=CN=CC=2)=NC=1N1C=CC=N1 MRBXWMSDNYIENV-UHFFFAOYSA-N 0.000 claims 1
- CUPVZRVESXKVLE-UHFFFAOYSA-N 5-chloro-4-n-ethyl-2-(4-pyridin-2-ylpyrazol-1-yl)pyrimidine-4,6-diamine Chemical compound NC1=C(Cl)C(NCC)=NC(N2N=CC(=C2)C=2N=CC=CC=2)=N1 CUPVZRVESXKVLE-UHFFFAOYSA-N 0.000 claims 1
- VZLNIQRTGKXZAX-UHFFFAOYSA-N 5-chloro-4-n-ethyl-2-(5-fluoroindazol-1-yl)pyrimidine-4,6-diamine Chemical compound NC1=C(Cl)C(NCC)=NC(N2C3=CC=C(F)C=C3C=N2)=N1 VZLNIQRTGKXZAX-UHFFFAOYSA-N 0.000 claims 1
- MTUZRJLBYWQACL-UHFFFAOYSA-N 5-chloro-4-n-ethyl-2-indazol-1-ylpyrimidine-4,6-diamine Chemical compound NC1=C(Cl)C(NCC)=NC(N2C3=CC=CC=C3C=N2)=N1 MTUZRJLBYWQACL-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- LKNYBALOJJKOGD-UHFFFAOYSA-N [1-[4-amino-5-bromo-6-(ethylamino)pyrimidin-2-yl]pyrazol-4-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(Br)C(NCC)=NC(N2N=CC(=C2)C(=O)N2CCOCC2)=N1 LKNYBALOJJKOGD-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000013066 combination product Substances 0.000 claims 1
- 229940127555 combination product Drugs 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 150000003852 triazoles Chemical group 0.000 claims 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61P11/00—Drugs for disorders of the respiratory system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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Claims (22)
1. Spoj formule (I):
[image]
,
naznačen time što:
– R1 se bira iz skupine koju čine vodik, halogen, cikloalkil i alkil s tri ili četiri atoma ugljika, nerazgranat ili razgranat;
– Y se bira iz skupine koju čine C-R2 i atom dušika;
– R2 se bira iz skupine koju čine:
(a) arilna ili heteroarilna skupina, koja može biti supstituirana s jednim ili više atoma halogena, ili s jednom ili više cikloalkilnih, hidroksi, (C1-C8) alkoksi, (C1-C8) alkiltio, amino, mono- ili dialkilamino, alkoksialkilnih, hidroksikarbonilnih i alkoksikarbonilnih skupina;
(b) alkoksikarbonilna skupina formule (-CO(R7), gdje R7 predstavlja hidroksilnu skupinu ili skupinu [-N(R8)(R9)];
R8 i R9 se neovisno bira iz skupine koju čine atom vodika, cikloalkil i alkil s tri ili četiri atoma ugljika, nerazgranat ili razgranat i može biti supstituiran s halogenom ili arilnom ili heterocikličkom skupinom;
ili R8 i R9, zajedno s atomom dušika na kojeg su vezani, tvore zasićeni pet- ili šesteročlani prsten, koji može sadržavati dodatni heteroatom, kojeg se bira iz skupine koju čine kisik i dušik, može biti supstituiran s (C1-C8) alkilnom skupinom;
– R3 se bira iz skupine koju čine vodik, halogen, cikloalkilna skupina i (C1-C8) alkilna skupina, nerazgranata ili razgranata, koja može biti supstituirana s atomima halogena;
ili R2 i R3, zajedno s atomima ugljika na kojeg su vezani, tvore šesteročlani arilni ili heteroarilni prsten, koji može biti supstituiran s jednim ili više atoma halogena, ili s jednom ili više skupina koje se bira između cikloalkila, hidroksi, (C1-C8) alkoksi, (C1-C8) alkiltio, amino, mono- ili dialkilamino, alkoksialkila, hidroksikarbonila i alkoksikarbonila;
– X se bira iz skupine koju čine atom halogena i cijano skupina;
– R4, R5 i R6 se neovisno bira iz skupine koju čine:
(a) atom vodika;
(b) alkilna, cikloalkilna ili cikloalkilalkilna skupina s najviše pet atoma ugljika, nerazgranata ili razgranata i može biti supstituirana s jednim ili više atoma halogena, metoksi skupina ili heteroarilnih skupina, gdje navedena heteroarilna skupina može biti supstituirana s atomima halogena ili (C1-C8) alkilnim skupinama;
(c) alilna ili propargilna skupina, koja može biti supstituirana s jednim ili više atoma halogena ili s jednom ili više skupina koje se bira iz skupine koju čine cikloalkil, hidroksi, (C1-C8) alkoksi, (C1-C8) alkiltio, amino, mono- ili dialkilamino, alkoksialkil, hidroksikarbonil i alkoksikarbonil; i
(d) tetrahidropiranilna skupina;
ili R5 i R6 mogu, zajedno s atomom dušika na kojeg su vezani, tvoriti pirazolni ili triazolni prsten, koji može biti supstituiran s atomima halogena
i njegove farmaceutski prihvatljive soli.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R4 predstavlja atom vodika.
3. Spoj u skladu s patentnim zahtjevom 2, naznačen time što R1, R3 i R5 predstavljaju atom vodika, X predstavlja atom broma, a Y predstavlja atom dušika.
4. Spoj u skladu s patentnim zahtjevom 3, naznačen time što se R6 bira iz skupine koju čine alkil, cikloalkilalkil i alkilcikloalkil, koji može biti supstituiran s metoksi skupinom ili heteroarilom, koji pak može biti supstituiran s (C1-C8) alkilnom skupinom.
5. Spoj u skladu s patentnim zahtjevom 4, naznačen time što se R6 bira iz skupine koju čine etil, propil, i ciklopropilmetil, od kojih sve mogu biti supstituirane s metoksi skupinom ili peteročlanom heteroarilnom skupinom, koja pak može biti supstituirana s jednom ili više metilnih skupina.
6. Spoj u skladu s patentnim zahtjevom 3, naznačen time što se R6 bira iz skupine koja se sastoji od skupine alil, propargil i tetrahidropiranil od kojih sve mogu biti supstituirane s alkilnom skupinom, nerazgranatom ili razgranatom, s najviše tri atoma ugljika.
7. Spoj u skladu s patentnim zahtjevom 2, naznačen time što R1, R3 i R5 predstavlja atom vodika, X predstavlja atom broma, Y predstavlja ostatak C-R2, a R2 predstavlja heteroarilnu skupinu, koja može biti supstituirana s atomima halogena.
8. Spoj u skladu s patentnim zahtjevom 7, naznačen time što R2 se bira između piridina, kinolina, pirimidina ili pirazina, koji su mogu biti supstituirani s atomima halogena.
9. Spoj u skladu s patentnim zahtjevom 8, naznačen time što se R6 bira iz skupine koju čine alkilna, cikloalkilalkilna i alkilcikloalkilna skupina, od kojih sve mogu biti supstituirane s metoksi skupinom ili s heteroarilnom skupinom, koja pak može biti supstituirana s (C1-C8) alkilnom skupinom.
10. Spoj u skladu s patentnim zahtjevom 8, naznačen time što se R6 bira iz skupine koju čine etil, propil, i ciklopropilmetil, koji može biti supstituiran s metoksi skupinom ili s peteročlanom heteroarilnom skupinom, koja može biti supstituirana s jednom ili više metilnih skupina.
11. Spoj u skladu s patentnim zahtjevom 8, naznačen time što se R6 bira iz skupine koju čine alilnu, propargilnu i tetrahidropiranilnu skupinu, koje mogu biti supstituirane s atomima halogena.
12. Spoj u skladu s patentnim zahtjevom 2, naznačen time što R1 i R5 predstavlja atom vodika, X predstavlja atom broma, Y predstavlja atom ugljika, a R2 i R3, zajedno s atomima ugljika na kojeg su vezani, tvore izborno supstituiranu arilnu ili heteroarilnu skupinu.
13. Spoj u skladu s patentnim zahtjevom 12, naznačen time što R2 i R3, zajedno s atomima ugljika na kojeg su vezani, tvore fenilni ili piridinski prsten, koji mogu biti supstituirani s atomima halogena.
14. Spoj u skladu s patentnim zahtjevom 13, naznačen time što se R6 bira iz skupine koju čine alkil, cikloalkilalkil i alkilcikloalkil, koji može biti supstituiran s metoksi skupinom ili heteroarilnom skupinom, koja pak može biti supstituirana s (C1-C8) alkilnom skupinom.
15. Spoj u skladu s patentnim zahtjevom 14, naznačen time što se R6 bira iz skupine koju čine etil, propil i ciklopropilmetil, može biti supstituiran s metoksi skupinom ili s peteročlanom heteroarilnom skupinom, koja može biti supstituirana s jednom ili više metilnih skupina.
16. Spoj u skladu s patentnim zahtjevom 13, naznačen time što se R6 bira iz skupine koju čine izborno supstituirani alil, propargil i tetrahidropiranil.
17. Spoj u skladu s patentnim zahtjevom 2, naznačen time što R1 i R5 predstavljaju atom vodika, X predstavlja atom broma, Y predstavlja ostatak CR2, R2 i R3, zajedno s atomima ugljika na koje su vezani, tvore fenilni ili piridinski prsten, a R6 se bira iz skupine koju čine etil, propil i ciklopropilmetil, koji može biti supstituiran s tiazolnim prstenom, koji može biti supstituiran s jednom ili više metilnih skupina.
18. Spoj u skladu s patentnim zahtjevom 2, naznačen time što R1, R3 i R5 predstavljaju atom vodika, X predstavlja atom broma, Y predstavlja atom dušika, a R6 se bira iz skupine koju čine etil, propil, propargil i ciklopropilmetil, koji može biti supstituiran s tiazolnim prstenom, koji pak može biti supstituiran s jednom ili više metilnih skupina.
19. Spoj u skladu s patentnim zahtjevom 1, naznačen time što se bira iz skupine koju čine:
5-brom-N4-(ciklopropilmetil)-2-(1H-indazol-1-il)pirimidin-4,6-diamin;
5-brom-N4-etil-2-(1H-indazol-1-il)pirimidin-4,6-diamin;
5-brom-2-(1H-indazol-1-il)-N4-(prop-2-inil)pirimidin-4,6-diamin;
5-brom-2-(1H-indazol-1-il)-6-(1H-pirazol-1-il)pirimidin-4-amin;
N4-[(1H-benzo[d]imidazol-2-il)metil]-5-brom-2-(1H-indazol-1-il)pirimidin-4,6-diamin;
5-brom-2-(1H-indazol-1-il)-N4-[(2-metiltiazol-4-il)metil]pirimidin-4,6-diamin;
5-brom-N4-(tetrahidro-2H-piran-4-il)-2-(1H-indazol-1-il)pirimidin-4,6-diamin;
5-brom-2-(1H-indazol-1-il)-N4-[(1-metil-1H-pirazol-4-il)metil]pirimidin-4,6-diamin;
5-brom-2-(1H-indazol-1-il)-N4-[(tiazol-5-il)metil]pirimidin-4,6-diamin;
5-brom-2-(1H-indazol-1-il)-N4-[(4-metiltiazol-5-il)metil]pirimidin-4,6-diamin;
5-brom-2-(1H-indazol-1-il)-N4-(2-metoksietil)pirimidin-4,6-diamin;
5-brom-N4-[(4-metiltiazol-5-il)metil]-2-(1H-pirazol-1-il)pirimidin-4,6-diamin;
5-brom-N4-(2-metoksietil)-2-(1H-pirazol-1-il)pirimidin-4,6-diamin;
N4-[(1H-benzo[d]imidazol-2-il)metil]-5-brom-2-(1H-pirazol-1-il)pirimidin-4,6-diamin;
5-brom-N4-(prop-2-inil)-2-[4-(piridin-4-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-2-(4-(piridin-4-il)-1H-pirazol-1-il)-N4-[(tiazol-5-il)metil]pirimidin-4,6-diamin;
5-brom-N4-(prop-2-inil)-2-[4-(piridin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-(ciklopropilmetil)-2-[4-(piridin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-[(4-metiltiazol-5-il)metil]-2-(4-(piridin-2-il)-1H-pirazol-1-il)pirimidin-4,6-diamin;
5-brom-2-[4-(piridin-2-il)-1H-pirazol-1-il]-N4-[(tiazol-5-il)metil]pirimidin-4,6-diamin;
5-brom-N4-(2-metoksietil)-2-[4-(piridin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-(prop-2-inil)-2-[4-(kinolin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-(tetrahidro-2H-piran-4-il)-2-[4-(kinolin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-[(2-metiltiazol-4-il)metil]-2-[4-(kinolin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-[(4-metiltiazol-5-il)metil]-2-[4-(kinolin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-etil-2-(4-fenil-1H-pirazol-1-il)pirimidin-4,6-diamin;
5-brom-2-[4-(4-klorfenil)-1H-pirazol-1-il]-N4-etilpirimidin-4,6-diamin;
5-brom-2-[4-(4-klorfenil)-1H-pirazol-1-il]-N4-(prop-2-inil)pirimidin-4,6-diamin;
5-brom-N4-[(4-metiltiazol-5-il)metil]-2-[4-(pirazin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-(prop-2-inil)-2-[4-(pirazin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-(prop-2-inil)-2-(1H-pirazolo[3,4-b]piridin-1-il)pirimidin-4,6-diamin;
5-brom-N4-[(4-metiltiazol-5-il)metil]-2-(1H-pirazolo[3,4-b]piridin-1-il)pirimidin-4,6-diamin;
5-brom-N4-(prop-2-inil)-2-(1H-pirazolo[3,4-c]piridin-1-il)pirimidin-4,6-diamin;
5-brom-N4-[(4-metiltiazol-5-il)metil]-2-(1H-pirazolo[3,4-c]piridin-1-il)pirimidin-4,6-diamin;
5-brom-N4-(ciklopropilmetil)-2-(1H-pirazolo[3,4-c]piridin-1-il)pirimidin-4,6-diamin;
5-brom-2-(1H-pirazolo[3,4-c]piridin-1-il)-N4-[(tiazol-5-il)metil]pirimidin-4,6-diamin;
5-brom-N4-(2-metoksietil)-2-(1H-pirazolo[3,4-c]piridin-1-il)pirimidin-4,6-diamin;
5-brom-N4-(prop-2-inil)-2-(1H-pirazolo[4,3-c]piridin-1-il)pirimidin-4,6-diamin;
5-brom-N4-[(4-metiltiazol-5-il)metil]-2-(1H-pirazolo[4,3-c]piridin-1-il)pirimidin-4,6-diamin;
5-brom-N4-(prop-2-inil)-2-(1H-pirazolo[4,3-b]piridin-1-il)pirimidin-4,6-diamin;
5-brom-N4-[(4-metiltiazol-5-il)metil]-2-(1H-pirazolo[4,3-b]piridin-1-il)pirimidin-4,6-diamin;
5-brom-N4-(prop-2-inil)-2-(1H-1,2,4-triazol-1-il)pirimidin-4,6-diamin;
5-brom-N4-[(4-metiltiazol-5-il)metil]-2-(1H-1,2,4-triazol-1-il)pirimidin-4,6-diamin;
5-brom-N4-(2-metoksietil)-2-(1H-1,2,4-triazol-1-il)pirimidin-4,6-diamin;
5-brom-N4-[(tiazol-5-il)metil]-2-(1H-1,2,4-triazol-1-il)pirimidin-4,6-diamin;
5-brom-N4-(ciklopropilmetil)-2-(1H-1,2,4-triazol-1-il)pirimidin-4,6-diamin;
1-[4-amino-5-brom-6-(prop-2-inilamino)pirimidin-2-il]-1H-pirazol-4-karboksilna kiselina;
1-[4-amino-5-brom-6-(etilamino)pirimidin-2-il]-1H-pirazol-4-karboksilna kiselina;
1-{4-[(4-metiltiazol-5-il)metilamino]-6-amino-5-brompirimidin-2-il}-1H-pirazol-4-karboksilna kiselina;
{1-[4-amino-5-brom-6-(etilamino)pirimidin-2-il]-1H-pirazol-4-il}(morfolino)metanon;
5-brom-6-(1H-pirazol-1-il)-2-[4-(piridin-4-il)-1H-pirazol-1-il]pirimidin-4-amin;
5-brom-6-(1H-pirazol-1-il)-2-[4-(piridin-2-il)-1H-pirazol-1-il]pirimidin-4-amin;
5-brom-2-[4-(pirazin-2-il)-1H-pirazol-1-il)-6-(1H-pirazol-1-il]pirimidin-4-amin;
5-brom-6-(1H-pirazol-1-il)-2-(1H-1,2,4-triazol-1-il)pirimidin-4-amin;
1-[4-(2-metoksietilamino)-6-amino-5-brompirimidin-2-il]-1H-pirazol-4-karboksilna kiselina;
1-[4-amino-5-brom-6-(ciklopropilmetilamino)pirimidin-2-il]-1H-pirazol-4-karboksilna kiselina;
1-[4-amino-5-brom-6-(isopropilamino)pirimidin-2-il]-1H-pirazol-4-karboksilna kiselina;
5-brom-N4-etil-2-[4-(piridin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-etil-2-[4-(pirimidin-4-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-etil-2-[4-(kinolin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-klor-N4-etil-2-[4-(piridin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-klor-N4-etil-2-(1H-indazol-1-il)pirimidin-4,6-diamin;
5-klor-N4-etil-2-(5-fluor-1H-indazol-1-il)pirimidin-4,6-diamin;
5-brom-N4-etil-2-(1H-indazol-1-il)-N6-(prop-2-inil)pirimidin-4,6-diamin;
5-brom-N4-(ciklopropilmetil)-2-(1H-indazol-1-il)-N6-(prop-2-inil)pirimidin-4,6-diamin;
5-brom-N4-(tetrahidro-2H-piran-4-il)-2-(1H-indazol-1-il)-N6-(prop-2-inil)pirimidin-4,6-diamin;
N4-[(1H-benzo[d]imidazol-2-il)metil]-5-brom-2-(1H-indazol-1-il)-N6-(prop-2-inil)pirimidin-4,6-diamin;
5-brom-N4-etil-N6-(prop-2-inil)-2-[4-(piridin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-(ciklopropilmetil)-N6-(prop-2-inil)-2-[4-(piridin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-(tetrahidro-2H-piran-4-il)-N6-(prop-2-inil)-2-[4-(piridin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
N4-[(1H-benzo[d]imidazol-2-il)metil]-5-brom-N6-(prop-2-inil)-2-[4-(piridin-2-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-etil-N6-(prop-2-inil)-2-[4-(pirimidin-4-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-(ciklopropilmetil)-N6-etil-2-[4-(pirimidin-4-il)-1H-pirazol-1-il]pirimidin-4,6-diamin;
5-brom-N4-etil-N6-(tetrahidro-2H-piran-4-il)-2-[4-(pirimidin-4-il)-1H-pirazol-1-il]pirimidin-4,6-diamin; i
N4-[(1H-benzo[d]imidazol-2-il)metil]-5-brom-N6-etil-2-[4-(pirimidin-4-il)-1H-pirazol-1-il]pirimidin-4,6-diamin.
20. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 19, zajedno s farmaceutski prihvatljivom pomoćnom tvari.
21. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 19, naznačen time što je namijenjen upotrebi u liječenju bolesti ili patološkom stanju podložnom poboljšanju inhibiranju fosfodiesteraze 10, gdje se bolest ili patološko stanje podložno poboljšanju inhibiranju fosfodiesteraze 10 bira iz skupine koju čine bolesti i patološka stanja središnjeg živčanog sustava, poput shizofrenije, Huntingtonove bolesti, Parkinsonove bolesti, Alzheimerove bolesti i depresije, te respiratorni poremećaji, poput plućne hipertenzije, astme i COPD-a.
22. Kombinacijski produkt, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 19, te najmanje još jedan lijek, gdje se navedeni lijek bira između lijekova korisni u liječenju bolesti središnjeg živčanog sustava, poput shizofrenije, Parkinsonove bolesti, Huntingtonove bolesti, Alzheimerove bolesti i depresije, te respiratornih poremećaja, poput plućne hipertenzije, astme i COPD-a.
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ES201330082A ES2480341B1 (es) | 2013-01-24 | 2013-01-24 | Nuevos derivados de pirimidina como inhibidores de la fosfodiesterasa 10 (PDE-10) |
EP14703553.9A EP2948443B1 (en) | 2013-01-24 | 2014-01-23 | New pyrimidine derivatives as phosphodiesterase 10 inhibitors (pde-10) |
PCT/EP2014/051290 WO2014114695A1 (en) | 2013-01-24 | 2014-01-23 | New pyrimidine derivatives as phosphodiesterase 10 inhibitors (pde-10) |
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EP (1) | EP2948443B1 (hr) |
JP (1) | JP6254194B2 (hr) |
KR (1) | KR101869144B1 (hr) |
CN (1) | CN105008346B (hr) |
AU (1) | AU2014209950B2 (hr) |
BR (1) | BR112015017678B1 (hr) |
CA (1) | CA2897260C (hr) |
CY (1) | CY1118552T1 (hr) |
DK (1) | DK2948443T3 (hr) |
EA (1) | EA026330B1 (hr) |
ES (2) | ES2480341B1 (hr) |
HR (1) | HRP20161495T1 (hr) |
HU (1) | HUE031831T2 (hr) |
LT (1) | LT2948443T (hr) |
ME (1) | ME02551B (hr) |
MX (1) | MX361160B (hr) |
PL (1) | PL2948443T3 (hr) |
PT (1) | PT2948443T (hr) |
RS (1) | RS55449B1 (hr) |
SI (1) | SI2948443T1 (hr) |
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CN107286146B (zh) * | 2017-07-05 | 2020-07-31 | 上海肇钰医药科技有限公司 | 作为腺苷a2a受体拮抗剂的4-氨基嘧啶衍生物及其用途 |
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US20080221103A1 (en) | 2007-03-09 | 2008-09-11 | Orchid Research Laboratories Ltd. | New heterocyclic compounds |
RU2531274C2 (ru) | 2009-05-07 | 2014-10-20 | Энвиво Фармасьютикалз, Инк. | Феноксиметильные гетероциклические соединения |
WO2010138430A1 (en) | 2009-05-27 | 2010-12-02 | Merck Sharp & Dohme Corp. | Alkoxy tetrahydro-pyridopyrimidine pde10 inhibitors |
JP6007102B2 (ja) | 2009-06-24 | 2016-10-12 | コーニンクレッカ フィリップス エヌ ヴェKoninklijke Philips N.V. | 画像情報に基づいた構造の輪郭の決定 |
AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
US8343970B2 (en) | 2010-03-12 | 2013-01-01 | Omeros Corporation | PDE10 inhibitors and related compositions and methods |
WO2011119518A1 (en) * | 2010-03-25 | 2011-09-29 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
ES2365960B1 (es) | 2010-03-31 | 2012-06-04 | Palobiofarma, S.L | Nuevos antagonistas de los receptores de adenosina. |
WO2011150156A2 (en) | 2010-05-26 | 2011-12-01 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
US8592423B2 (en) | 2011-06-21 | 2013-11-26 | Bristol-Myers Squibb Company | Inhibitors of PDE10 |
WO2013052395A1 (en) * | 2011-10-06 | 2013-04-11 | Merck Sharp & Dohme Corp. | 1,3-substituted azetidine pde10 inhibitors |
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2013
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2014
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- 2014-01-23 PL PL14703553T patent/PL2948443T3/pl unknown
- 2014-01-24 US US14/762,655 patent/US9447095B2/en active Active
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2016
- 2016-11-11 HR HRP20161495TT patent/HRP20161495T1/hr unknown
- 2016-11-23 SM SM201600428T patent/SMT201600428B/it unknown
- 2016-11-23 CY CY20161101206T patent/CY1118552T1/el unknown
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