HRP20130867T1 - Kondenzirani heterocikliäśki spojevi 2-cijanofenila, te njihovi pripravci i uporaba - Google Patents
Kondenzirani heterocikliäśki spojevi 2-cijanofenila, te njihovi pripravci i uporaba Download PDFInfo
- Publication number
- HRP20130867T1 HRP20130867T1 HRP20130867AT HRP20130867T HRP20130867T1 HR P20130867 T1 HRP20130867 T1 HR P20130867T1 HR P20130867A T HRP20130867A T HR P20130867AT HR P20130867 T HRP20130867 T HR P20130867T HR P20130867 T1 HRP20130867 T1 HR P20130867T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyrido
- pyrimidin
- dihydro
- benzonitrile
- methyl
- Prior art date
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- -1 2-cyanophenyl Chemical group 0.000 title claims 15
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 4
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 4
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 4
- 208000037765 diseases and disorders Diseases 0.000 claims 4
- 230000000155 isotopic effect Effects 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 4
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 3
- 229910006069 SO3H Inorganic materials 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004442 acylamino group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000005945 imidazopyridyl group Chemical group 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 3
- 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- RFCAFNGQFYTNPB-LJQANCHMSA-N (3r)-3-[[6-(4-chloro-2-cyanophenyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]-3-(6-methoxypyridin-3-yl)propanoic acid Chemical compound C1=NC(OC)=CC=C1[C@@H](CC(O)=O)NC1=NC=NC2=C1CN(C=1C(=CC(Cl)=CC=1)C#N)CC2 RFCAFNGQFYTNPB-LJQANCHMSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000003251 Pruritus Diseases 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 208000009935 visceral pain Diseases 0.000 claims 2
- ZAQCLAWVZDLXFA-JOCHJYFZSA-N (3r)-3-[[6-(2-cyano-4-methylphenyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]-3-(6-methoxypyridin-3-yl)-n,n-dimethylpropanamide Chemical compound C1=NC(OC)=CC=C1[C@@H](CC(=O)N(C)C)NC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 ZAQCLAWVZDLXFA-JOCHJYFZSA-N 0.000 claims 1
- HVJRUCHDMRKOFD-HXUWFJFHSA-N (3r)-3-[[6-(2-cyano-4-methylphenyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]-3-(6-methoxypyridin-3-yl)propanoic acid Chemical compound C1=NC(OC)=CC=C1[C@@H](CC(O)=O)NC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 HVJRUCHDMRKOFD-HXUWFJFHSA-N 0.000 claims 1
- XPCVTIPTPXJKOD-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-ylmethylamino)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C=C4OCOC4=CC=3)N=CN=C2CC1 XPCVTIPTPXJKOD-UHFFFAOYSA-N 0.000 claims 1
- XSSBBWWYALHHHM-UHFFFAOYSA-N 2-[4-(1,3-benzoxazol-5-ylmethylamino)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C=C4N=COC4=CC=3)N=CN=C2CC1 XSSBBWWYALHHHM-UHFFFAOYSA-N 0.000 claims 1
- BEWVSTIRWSWSRV-UHFFFAOYSA-N 2-[4-(1h-indol-6-ylmethylamino)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C=C4NC=CC4=CC=3)N=CN=C2CC1 BEWVSTIRWSWSRV-UHFFFAOYSA-N 0.000 claims 1
- QYKQWICOAQCEFR-UHFFFAOYSA-N 2-[4-(imidazo[1,2-a]pyridin-7-ylmethylamino)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC3=CC4=NC=CN4C=C3)N=CN=C2CC1 QYKQWICOAQCEFR-UHFFFAOYSA-N 0.000 claims 1
- LJLPOPGWBVSIFR-UHFFFAOYSA-N 2-[4-[(2-methoxypyrimidin-5-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C1=NC(OC)=NC=C1CNC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 LJLPOPGWBVSIFR-UHFFFAOYSA-N 0.000 claims 1
- OQZFQIHVHFJDIX-UHFFFAOYSA-N 2-[4-[(3,5-dichloropyridin-2-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C(=CC(Cl)=CN=3)Cl)N=CN=C2CC1 OQZFQIHVHFJDIX-UHFFFAOYSA-N 0.000 claims 1
- XTKCRIWRHDIPGK-UHFFFAOYSA-N 2-[4-[(3-cyanophenyl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C=C(C=CC=3)C#N)N=CN=C2CC1 XTKCRIWRHDIPGK-UHFFFAOYSA-N 0.000 claims 1
- NTNQBRZBMXLLSB-UHFFFAOYSA-N 2-[4-[(3-fluoro-4-methylphenyl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C=C(F)C(C)=CC=3)N=CN=C2CC1 NTNQBRZBMXLLSB-UHFFFAOYSA-N 0.000 claims 1
- AFYIVHVQSPKIIO-UHFFFAOYSA-N 2-[4-[(3-iodo-4-methylphenyl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C=C(I)C(C)=CC=3)N=CN=C2CC1 AFYIVHVQSPKIIO-UHFFFAOYSA-N 0.000 claims 1
- UKVBYTFAVWLLPI-UHFFFAOYSA-N 2-[4-[(4-amino-2-methoxypyrimidin-5-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound NC1=NC(OC)=NC=C1CNC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 UKVBYTFAVWLLPI-UHFFFAOYSA-N 0.000 claims 1
- RCAMJYBTCSWONV-UHFFFAOYSA-N 2-[4-[(4-amino-2-methylpyrimidin-5-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C(=NC(C)=NC=3)N)N=CN=C2CC1 RCAMJYBTCSWONV-UHFFFAOYSA-N 0.000 claims 1
- GJNGWVFEUIDZQY-UHFFFAOYSA-N 2-[4-[(4-chloro-3-methylsulfonylphenyl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C=C(C(Cl)=CC=3)S(C)(=O)=O)N=CN=C2CC1 GJNGWVFEUIDZQY-UHFFFAOYSA-N 0.000 claims 1
- FZGBLBWJZIIIIW-UHFFFAOYSA-N 2-[4-[(5-chloropyridin-2-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3N=CC(Cl)=CC=3)N=CN=C2CC1 FZGBLBWJZIIIIW-UHFFFAOYSA-N 0.000 claims 1
- UZBQPRXVKUBNPY-UHFFFAOYSA-N 2-[4-[(5-cyclopropylpyridin-2-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3N=CC(=CC=3)C3CC3)N=CN=C2CC1 UZBQPRXVKUBNPY-UHFFFAOYSA-N 0.000 claims 1
- QTXDILFONAWWKU-UHFFFAOYSA-N 2-[4-[(6-chloropyridin-3-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C=NC(Cl)=CC=3)N=CN=C2CC1 QTXDILFONAWWKU-UHFFFAOYSA-N 0.000 claims 1
- NWXLZEXLJBKNDM-UHFFFAOYSA-N 2-[4-[(6-ethylpyridin-3-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C1=NC(CC)=CC=C1CNC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 NWXLZEXLJBKNDM-UHFFFAOYSA-N 0.000 claims 1
- RVOHPYXQEZNVMH-UHFFFAOYSA-N 2-[4-[(6-methoxypyridin-3-yl)methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C1=NC(OC)=CC=C1CNC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 RVOHPYXQEZNVMH-UHFFFAOYSA-N 0.000 claims 1
- PFTSILFRTYLFOO-UHFFFAOYSA-N 2-[4-[1-(1,3-benzodioxol-5-yl)ethylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C=1C=C2OCOC2=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N PFTSILFRTYLFOO-UHFFFAOYSA-N 0.000 claims 1
- IUVDXBRGFXCMBT-UHFFFAOYSA-N 2-[4-[1-(4-chloro-3-methylsulfonylphenyl)ethylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C=1C=C(Cl)C(S(C)(=O)=O)=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N IUVDXBRGFXCMBT-UHFFFAOYSA-N 0.000 claims 1
- PFTSILFRTYLFOO-MRXNPFEDSA-N 2-[4-[[(1r)-1-(1,3-benzodioxol-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N([C@H](C)C=1C=C2OCOC2=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N PFTSILFRTYLFOO-MRXNPFEDSA-N 0.000 claims 1
- IUVDXBRGFXCMBT-MRXNPFEDSA-N 2-[4-[[(1r)-1-(4-chloro-3-methylsulfonylphenyl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N([C@H](C)C=1C=C(C(Cl)=CC=1)S(C)(=O)=O)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N IUVDXBRGFXCMBT-MRXNPFEDSA-N 0.000 claims 1
- LBYHKHGKXHAAOR-LJQANCHMSA-N 2-[4-[[(1r)-1-[6-(difluoromethyl)pyridin-3-yl]-3-hydroxypropyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(N[C@H](CCO)C=3C=NC(=CC=3)C(F)F)N=CN=C2CC1 LBYHKHGKXHAAOR-LJQANCHMSA-N 0.000 claims 1
- PXQXKFDRXQKIIW-HXUWFJFHSA-N 2-[4-[[(1r)-3-hydroxy-1-(6-methoxypyridin-3-yl)propyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C1=NC(OC)=CC=C1[C@@H](CCO)NC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 PXQXKFDRXQKIIW-HXUWFJFHSA-N 0.000 claims 1
- WDRMEYJAYGWMTR-OAQYLSRUSA-N 2-[4-[[(1r)-3-hydroxy-1-(6-methylpyridin-3-yl)propyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(N[C@H](CCO)C=3C=NC(C)=CC=3)N=CN=C2CC1 WDRMEYJAYGWMTR-OAQYLSRUSA-N 0.000 claims 1
- MPEWWUPGWDTWHF-LJQANCHMSA-N 2-[4-[[(1r)-3-hydroxy-1-[6-(trifluoromethyl)pyridin-3-yl]propyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(N[C@H](CCO)C=3C=NC(=CC=3)C(F)(F)F)N=CN=C2CC1 MPEWWUPGWDTWHF-LJQANCHMSA-N 0.000 claims 1
- PFTSILFRTYLFOO-INIZCTEOSA-N 2-[4-[[(1s)-1-(1,3-benzodioxol-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N([C@@H](C)C=1C=C2OCOC2=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N PFTSILFRTYLFOO-INIZCTEOSA-N 0.000 claims 1
- OSQOURHXWJQPNS-HNNXBMFYSA-N 2-[4-[[(1s)-1-(2-methoxypyrimidin-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C1=NC(OC)=NC=C1[C@H](C)NC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 OSQOURHXWJQPNS-HNNXBMFYSA-N 0.000 claims 1
- IUVDXBRGFXCMBT-INIZCTEOSA-N 2-[4-[[(1s)-1-(4-chloro-3-methylsulfonylphenyl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N([C@@H](C)C=1C=C(C(Cl)=CC=1)S(C)(=O)=O)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N IUVDXBRGFXCMBT-INIZCTEOSA-N 0.000 claims 1
- BMCTVDCQKVLDDX-HXUWFJFHSA-N 2-[4-[[(1s)-1-[6-(difluoromethyl)pyridin-3-yl]-2-hydroxyethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(N[C@H](CO)C=3C=NC(=CC=3)C(F)F)N=CN=C2CC1 BMCTVDCQKVLDDX-HXUWFJFHSA-N 0.000 claims 1
- QNHMPCGUVCJNLG-LJQANCHMSA-N 2-[4-[[(1s)-2-hydroxy-1-(2-methoxypyrimidin-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound C1=NC(OC)=NC=C1[C@@H](CO)NC1=NC=NC2=C1CN(C=1C(=CC(C)=CC=1)C#N)CC2 QNHMPCGUVCJNLG-LJQANCHMSA-N 0.000 claims 1
- HDTMYJRQEISETD-HXUWFJFHSA-N 2-[4-[[(1s)-2-hydroxy-1-(2-methylpyrimidin-5-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(N[C@H](CO)C=3C=NC(C)=NC=3)N=CN=C2CC1 HDTMYJRQEISETD-HXUWFJFHSA-N 0.000 claims 1
- RXZNFBASJKIFOC-LJQANCHMSA-N 2-[4-[[(1s)-2-hydroxy-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(N[C@H](CO)C=3C=NC(=CC=3)C(F)(F)F)N=CN=C2CC1 RXZNFBASJKIFOC-LJQANCHMSA-N 0.000 claims 1
- OHKYSCNGLWLOFA-OAQYLSRUSA-N 2-[4-[[(1s)-2-methoxy-1-(6-methoxypyridin-3-yl)ethyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N([C@H](COC)C=1C=NC(OC)=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=C1C#N OHKYSCNGLWLOFA-OAQYLSRUSA-N 0.000 claims 1
- MPEWWUPGWDTWHF-IBGZPJMESA-N 2-[4-[[(1s)-3-hydroxy-1-[6-(trifluoromethyl)pyridin-3-yl]propyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(N[C@@H](CCO)C=3C=NC(=CC=3)C(F)(F)F)N=CN=C2CC1 MPEWWUPGWDTWHF-IBGZPJMESA-N 0.000 claims 1
- MPEWWUPGWDTWHF-UHFFFAOYSA-N 2-[4-[[3-hydroxy-1-[6-(trifluoromethyl)pyridin-3-yl]propyl]amino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NC(CCO)C=3C=NC(=CC=3)C(F)(F)F)N=CN=C2CC1 MPEWWUPGWDTWHF-UHFFFAOYSA-N 0.000 claims 1
- KVPJWYRZJZEFAA-UHFFFAOYSA-N 2-[4-[[4-chloro-3-(1,2,4-triazol-4-yl)phenyl]methylamino]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl]-5-methylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1N1CC2=C(NCC=3C=C(C(Cl)=CC=3)N3C=NN=C3)N=CN=C2CC1 KVPJWYRZJZEFAA-UHFFFAOYSA-N 0.000 claims 1
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Claims (33)
1. Spoj prema formuli 1:
[image]
naznačen time da
R1 je cikloalkil, cikloheteroalkil, aril ili heteroaril nesupstituiran ili supstituiran sa jednom ili više R4 skupina; ili
kada R1 je supstituiran i odabran od kinolinila, izokinolinila, kinoksalina, metilendioksifenila, imidazopiridila, benzoksazolila, i indolila, tada je R1 supstituiran sa Me, Et, Pr, izo-Pr, Ph, Cl, F, Br, CN, OH, OMe, OEt, OPh, COPh, CO2Me, CH2-N-morfolino, CH2-N-(4-Me-piperidino), NH2, CONH2, CF3, CHF2, OCF3, OCHF2, t-Bu, SMe, CH=CH-CO2H, SOMe, SO2Me, SO2CF3, SO2NH2, SO3H, SO3Me, ciklopropilom; ili
kada R1 je
[image]
tada je indeks n' odabran od 1-5 i svaki R5 je neovisno odabran iz skupine koja sadrži vodik, supstituiran ili nesupstituiran alkil, supstituiran ili nesupstituiran acil, supstituiran ili nesupstituiran acilamino, supstituiran ili nesupstituiran alkilamino, supstituiran ili nesupstituiran alkiltio, supstituiran ili nesupstituiran alkoksi, ariloksi, alkoksikarbonil, supstituiran alkoksikarbonil, supstituiran ili nesupstituiran alkilarilamino, arilalkiloksi, supstituiran arilalkiloksi, amino, aril, supstituiran aril, arilalkil, sulfo, supstituiran sulfo, supstituiran sulfonil, supstituiran sulfinil, supstituiran sulfanil, azido, supstituiran ili nesupstituiran karbamoil, karboksil, cijano, supstituiran ili nesupstituiran cikloalkil, supstituiran ili nesupstituiran cikloheteroalkil, supstituiran ili nesupstituiran dialkilamino, halo, heteroariloksi, supstituiran ili nesupstituiran heteroaril, supstituiran ili nesupstituiran heteroalkil, hidroksi, nitro, i tiol;
R2 je H, supstituiran ili nesupstituiran C1-C6 alkil ili cikloalkil;
svaki R3 i R4 je neovisno odabran iz skupine koja sadrži H, alkil, acil, acilamino, alkilamino, alkiltio, alkoksi, alkoksikarbonil, alkilarilamino, arilalkiloksi, amino, aril, arilalkil, sulfo, supstituiran sulfo, supstituiran sulfonil, supstituiran sulfinil, supstituiran sulfanil, azido, karbamoil, karboksil, cijano, cikloalkil, cikloheteroalkil, dialkilamino, halo, heteroariloksi, heteroaril, heteroalkil, hidroksi, nitro, i tiol;
m je 1, 2, 3 ili 4; ili R3 je supstituiran alkil;
ili farmaceutski prihvatljiva sol, solvat, tautomer ili njihova izotopna varijanta.
2. Spoj prema formuli 2:
[image]
naznačen time da
R1, R2 i R4, R5 su kao u zahtjevu 1; i
R3 je halo, supstituiran ili nesupstituiran C1-C6 alkil ili cikloalkil;
ili farmaceutski prihvatljiva sol, solvat, tautomer ili njihova izotopna varijanta.
3. Enantiomerno čist spoj prema zahtjevu 2 prema formuli 3a ili 3b:
[image]
naznačen time da
R1, R2 i R4, R5 su kao u zahtjevu 1; i
R3 je halo, supstituiran ili nesupstituiran C1-C6 alkil ili cikloalkil;
ili farmaceutski prihvatljiva sol, solvat, tautomer ili njihova izotopna varijanta.
4. Spoj prema bilo kojem zahtjevu od 1-3, naznačen time da R1 je supstituiran ili nesupstituiran aril ili heteroaril.
5. Spoj prema bilo kojem zahtjevu od 1-3, naznačen time da R1 je supstituiran ili nesupstituiran bicikloaril, bicikloalkil, ili bicikloheteroaril.
6. Spoj prema bilo kojem zahtjevu od 1-3, naznačen time da R1 je nesupstituiran fenil, piridil ili pirimidinil.
7. Spoj prema bilo kojem zahtjevu od 1-3, naznačen time da R1 je odabran od nesupstituiranog kinolinila, izokinolinila, kinoksalina, metilendioksifenila, imidazopiridila, benzoksazolila, te indolila.
8. Spoj prema bilo kojem zahtjevu od 1-3, naznačen time da R1 je odabran od kinolinila, izokinolinila, kinoksalina, metilendioksifenila, imidazopiridila, benzoksazolila, i indolila, supstituiranih sa Me, Et, Pr, izo-Pr, Ph, Cl, F, Br, CN, OH, OMe, OEt, OPh, COPh, CO2Me, CH2-N-morfolino, CH2-N-(4-Me-piperidino), NH2, CONH2, CF3, CHF2, OCF3, OCHF2, t-Bu, SMe, CH=CH-CO2H, SOMe, SO2Me, SO2CF3, SO2NH2, SO3H, SO3Me, ciklopropilom.
9. Spoj prema bilo kojem zahtjevu od 1-3, naznačen time da R1 je
[image]
i pri čemu je indeks n' odabran od 1-5 i svaki R5 je neovisno odabran iz skupine koja sadrži vodik, supstituiran ili nesupstituiran alkil, supstituiran ili nesupstituiran acil, supstituiran ili nesupstituiran acilamino, supstituiran ili nesupstituiran alkilamino, supstituiran ili nesupstituiran alkiltio, supstituiran ili nesupstituiran alkoksi, ariloksi, alkoksikarbonil, supstituiran alkoksikarbonil, supstituiran ili nesupstituiran alkilarilamino, arilalkiloksi, supstituiran arilalkiloksi, amino, aril, supstituiran aril, arilalkil, sulfo, supstituiran sulfo, supstituiran sulfonil, supstituiran sulfinil, supstituiran sulfanil, azido, supstituiran ili nesupstituiran karbamoil, karboksil, cijano, supstituiran ili nesupstituiran cikloalkil, supstituiran ili nesupstituiran cikloheteroalkil, supstituiran ili nesupstituiran dialkilamino, halo, heteroariloksi, supstituiran ili nesupstituiran heteroaril, supstituiran ili nesupstituiran heteroalkil, hidroksi, nitro, i tiol.
10. Spoj prema zahtjevu 9, naznačen time da indeks n' je 1, 2 ili 3.
11. Spoj prema zahtjevu 9, naznačen time da indeks n' je 1 ili 2.
12. Spoj prema bilo kojem zahtjevu od 9-11, naznačen time da svaki R5 je neovisno odabran od H, Me, Et, Pr, izo-Pr, Ph, Cl, F, Br, CN, OH, OMe, OEt, OPh, COPh, CO2Me, CH2-N-morfolino, CH2-N-(4-Me-piperidino), NH2, CONH2, CF3, CHF2, OCF3, OCHF2, t-Bu, SMe, CH=CH-CO2H, SOMe, SO2Me, SO2CF3, SO2NH2, SO3H, SO3Me, ciklopropila, triazolila, morfolinila, i piridila.
13. Spoj prema zahtjevu 1, naznačen time da spoj je prema formuli 4a, 4b, ili 4c:
[image]
i pri čemu R2 je kao u zahtjevu 1; R3 je kao u zahtjevu 2; i R5 kao u zahtjevu 9.
14. Spoj prema bilo kojem zahtjevu od 9-13, naznačen time da svaki R5 je neovisno odabran od H, Me, Et, Pr, izo-Pr, Ph, Cl, F, CN, OH, OMe, OEt, OPh, CF3, CHF2, OCF3, OCHF2, t-Bu, SO2Me, SO2CF3, i SO3Me.
15. Spoj prema bilo kojem zahtjevu od 9-13, naznačen time da R5 je H, Cl, F, Me, CF3, ili OMe.
16. Spoj prema bilo kojem zahtjevu od 1-15, naznačen time da R2 je odabran od H, Me, Et, n-Pr, t-Bu, CF3, CH2OH, CH2CH2OH, CH2CH2OAc, CH2(CH2)2OH, CH2CH2NHMe, CH2NMe2, CH2CH2NMe2, CH2CONH2, CH2CONMe2, CH2COOH, CH2CH2COOH, CH2(CH2)2COOH, CH2OMe, i CH2CH2OMe.
17. Spoj prema bilo kojem zahtjevu od 1-15, naznačen time da R2 je odabran od CH2NR2'R2", CH2CH2NR2'R2", i CH2CH2CH2NR2'R2"; i pri čemu R2' i R2" se mogu spojiti da tvore heterociklički prsten.
18. Spoj prema bilo kojem zahtjevu od 1-15, naznačen time da je R2 odabran od ciklopropila, ciklobutila ili cikloheksila.
19. Spoj prema bilo kojem zahtjevu od 1-15, naznačen time da R2 je Me.
20. Spoj prema bilo kojem zahtjevu od 1-15, naznačen time da R2 je CH2OH ili CH2CH2OH.
21. Spoj prema bilo kojem zahtjevu od 1-20, naznačen time da je R3 supstituiran ili nesupstituiran alkil.
22. Spoj prema bilo kojem zahtjevu od 1-20, naznačen time da R3 je Me ili CF3.
23. Spoj prema bilo kojem zahtjevu od 1-20, naznačen time da R3 je halo.
24. Spoj prema bilo kojem zahtjevu od 1-20, naznačen time da R3 je Cl.
25. Spoj prema zahtjevu 1, naznačen time da spoj je prema formuli 5a, 5b, ili 5c:
[image]
i pri čemu R2 je kao u zahtjevu 1; i R5 kao u zahtjevu 9.
26. Spoj prema zahtjevu 25, naznačen time da R2 je H, Me, Et, CH2OH, ili CH2CH2OH.
27. Spoj prema zahtjevu 25, naznačen time da R5 je H, Cl, F, Me, CF3, ili OMe.
28. Spoj prema zahtjevu 1, naznačen time da je odabran iz skupine koja sadrži:
5-Metil-2-{4-[(6-trifluorometil-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Bromo-2-{4-[(6-trifluorometil-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il -benzonitril;
5-Ciklopropil-2-{4-[(6-trifluorometil-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Kloro-2-{4-[(6-trifluorometil-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Trifluorometil-2-{4-[(6-trifluorometil-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Bromo-2-{4-[(R)-1-(6-trifluorometil-piridin-3-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Metil-2-{4-[(R)-1-(6-trifluorometil-piridin-3-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Kloro-2-{4-[(R)-1-(6-trifluorometil-piridin-3-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Fluoro-2-{4-[(6-trifluorometil-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2-{4-[(6-Trifluorometil-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Kloro-2-{4-[(2-metil-6-trifluorometil-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Kloro-2-{4-[(6-dimetilamino-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Kloro-2-{4-[(6-metoksi-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Bromo-2-{4-[(6-metoksi-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2-{4-[(6-Metoksi-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
5-Kloro-2-{4-[(3-kloro-5-trifluorometil-piridin-2-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Kloro-2-{4-[(5-trifluorometil-piridin-2-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
tert-butil ester (R)-3-[6-(4-Kloro-2-cijano-fenil)-5,6,7,8-tetrahidro-pirido[4,3-d]pirimidin-4-ilamino]-3-(6-metoksi-piridin-3-il)-propionske kiseline;
(R)-3-[6-(4-Kloro-2-cijano-fenil)-5,6,7,8-tetrahidro-pirido[4,3-d]pirimidin-4-ilamino]-3-(6-metoksi-piridin-3-il)-propionska kiselina;
5-Kloro-2-{4-[(R)-3-hidroksi-1-(6-trifluorometil-piridin-3-il)-propilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2- {4-[(R)-3-Hidroksi-1-(6-metil-piridin-3-il)-propilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2- {4-[(R)-1-(6-Difluorometil-piridin-3-il)-3-hidroksi-propilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[(S)-2-Hidroksi-1-(6-metoksi-piridin-3-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirinfdin-6-il}-5-metil-benzonitril;
2-{4-[(R)-3-Hidroksi-1-(6-metoksi-piridin-3-il)-propilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[3-Hidroksi-1-(6-trifluorometil-piridin-3-il)-propilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[(S)-2-Metoksi-1-(6-metoksi-piridin-3-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[(6-Kloro-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2- {4-[(5-Kloro-piridin-2-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
5-Metil-2-{4-[(piridin-2-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2-{4-[(5-Ciklopropil-piridin-2-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[(4-Amino-2-metil-pirimidin-5-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[(3,5-Dikloro-piridin-2-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[(6-Etil-piridin-3-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
5-Kloro-2-{4-[(R)-3-hidroksi-1-(6-metoksi-piridin-3-il)-propilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Kloro-2-{4-[(S)-2-hidroksi-1-(6-metoksi-piridin-3-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2-[4-(3-Cijano-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-5-metilbenzonitril;
2-{4-[(Imidazo[1,2-a]piridin-7-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[(Benzooksazol-5-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
5-Metil-2-{4-[(2-metil-pirimidin-5-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Metil-2-[4-(4-metil-3-[1,2,4]triazol-1-il-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-benzonitril;
(R)-3-[6-(2-Cijano-4-metil-fenil)-5,6,7,8-tetrahidro-pirido[4,3-d]pirimidin-4-ilamino]-3-(6-metoksi-piridin-3-il)-propionska kiselina;
(R)-3-[6-(2-Cijano-4-metil-fenil)-5,6,7,8-tetrahidro-pirido[4,3d]pirimidin-4-ilamino]-3-(6-metoksi-piridin-3-il)-propionamid;
(R)-3-[6-(2-Cijano-4-metil-fenil)-5,6,7,8-tetrahidro-pirido[4,3-d]pirimidin-4-ilamino]-3-(6-metoksi-piridin-3-il)-N,N-dimetil-propionamid;
5-Kloro-2-{4-[(imidazo[1,2-a]piridin-7-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Kloro-2-{4-[(2-metil-pirimidin-5-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2-{4-[(S)-2-Hidroksi-1-(6-trifluorometil-piridin-3-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
5-Kloro-2-{4-[(S)-2-hidroksi-1-(6-trifluorometil-piridin-3-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2-[4-(3-Fluoro-4-metil-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-5-metil-benzonitril;
5-Metil-2-[4-(4-metil-3-metilsulfanil-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-benzonitril;
2-[4-(4-Kloro-3-[1,2,4]triazol-4-il-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-5-metil-benzonitril;
5-Kloro-2-[4-(3-[1,2,4]triazol-4-il-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-benzonitril;
5-Kloro-2-[4-(4-kloro-3-[1,2,4]triazol-4-il-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-benzonitril;
5-Metil-2-[4-(3-[1,2,4]triazol-4-il-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-benzonitril;
2-{4-[(4-Amino-2-metoksi-pirimidin-5-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-[4-(3-Jodo-4-metil-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-5-metil-benzonitril;
5-Kloro-2-{4-[(R)-1-(2-metoksi-pirimidin-5-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2-{4-[(R)-1-(2-Metoksi-pirimidin-5-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-[4-(3-Metansulfonil-4-metil-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-5-metil-benzonitril;
2-{4-[(S)-2-Hidroksi-1-(2-metoksi-pirimidin-5-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[(2-Izopropil-pirimidin-5-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
5-Kloro-2-{4-[(R)-1-(6-difluorometil-piridin-3-il)-3-hidroksi-propilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Metil-2-[4-(4-metil-3-morfolin-4-il-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-benzonitril;
2-{4-[(R)-3-Hidroksi-1-(6-trifluorometil-piridin-3-il)-propilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[(S)-3-Hidroksi-1-(6-trifluorometil-piridin-3-il)-propilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
5-Metil-2-{4-[(R)-1-(2-metil-pirimidin-5-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Metil-2-{4-[(S)-1-(2-metil-pirimidin-5-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2-{4-[(2-Metoksi-pirimidin-5-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
5-Kloro-2-{4-[(2-metoksi-pirimidin-5-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2-{4-[(S)-1-(6-Difluorometil-piridin-3-il)-2-hidroksi-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-[4-(4-Kloro-3-metansulfonil-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-5-metil-benzonitril;
5-Kloro-2-{4-[(S)-1-(6-difluorometil-piridin-3-il)-2-hidroksi-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Kloro-2-{4-[(S)-2-hidroksi-1-(2-metil-pirimidin-5-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2-{4-[(S)-2-Hidroksi-1-(2-metil-pirimidin-5-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
5-Kloro-2-{4-[(R)-1-(2-metil-pirimidin-5-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Kloro-2-[4-(3-metansulfonil-4-metil-benzilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-benzonitril;
propil ester (R)-3-[6-(2-cijano-4-metil-fenil)-5,6,7,8-tetrahidro-pirido[4,3-d]pirimidin-4-ilamino]-3-(6-trifluorometil-piridin-3-il) octene kiseline
5-Kloro-2-{4-[(S)-2-hidroksi-1-(2-metoksi-pirimidin-5-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Metil-2-{4-[(kinoksalin-6-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Metil-2-{4-[(kinolin-2-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2- {4-[(1H-Indol-6-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[(Benzo[1,3]dioksol-5-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-[4-(1-Benzo[1,3]dioksol-5-il-etilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-5-metil-benzonitril;
5-Kloro-2-{4-[(kinoksalin-6-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
5-Metil-2-[4-(1-pirazin-2-il-etilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-benzonitril;
5-Metil-2-[4-(1-kinoksalin-6-il-etilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-benzonitril;
2-{4-[(S)-1-(2-Metoksi-pirimidin-5-il)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[1-(4-Kloro-3-metansulfonil-fenil)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-[4-((R)-1-Benzo[1,3]dioksol-5-il-etilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-5-metil-benzonitril;
2-[4-((S)-1-Benzo[1,3]dioksol-5-il-etilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-5-metil-benzonitril;
2-{4-[1-(3-Metansulfonil-4-metil-fenil)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
5-Metil-2-{4-[(kinolin-7-ilmetil)-amino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-benzonitril;
2-{4-[(R)-1-(4-Kloro-3-metansulfonil-fenil)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
2-{4-[(S)-1-(4-Kloro-3-metansulfonil-fenil)-etilamino]-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-5-metil-benzonitril;
5-Metil-2-[4-((R)-1-kinoksalin-6-il-etilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-benzonitril; i
5-Metil-2-[4-((S)-1-kinoksalin-6-il-etilamino)-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-benzonitril;
ili farmaceutski prihvatljiva sol, solvat, stereoizomer, tautomer ili njihova izotopna varijanta.
29. Farmaceutski pripravak naznačen time da sadrži farmaceutski prihvatljiv nosač i farmaceutski učinkovitu količinu spoja prema bilo kojem zahtjevu od 1-28.
30. Spoj prema bilo kojem zahtjevu od 1-28, naznačen time da je za uporabu kao farmaceutski pripravak.
31. Spoj prema bilo kojem zahtjevu od 1-28, naznačen time da je za uporabu u postupku za liječenja ili sprečavanja bolesti ili stanja odabranog od: boli uključujući akutnu, upalnu i neuropatsku bol, kroničnu bol, zubobolju i glavobolju uključujući migrenu, cluster glavobolje i glavobolje tenzijskog tipa, Parkinsonove bolesti, te multiple skleroze; bolesti i poremećaja koji su posredovani ili rezultiraju sa neuroupalom, traumatskom ozljedom mozga, te encefalitisom; centralno posredovanih neuropsihijatrijskih bolesti i poremećaja, depresivne manije, bipolarne bolesti, anksioznosti, shizofrenije, poremećaja prehrane, poremećaja spavanja i spoznajnih poremećaja; disfunkcije prostate, mokraćnog mjehura i crijeva, urinarne inkontinencije, oklijevanja kod mokrenja, rektalne preosjetljivosti, fekalne inkontinencije, benigne hipertrofije prostate i upalne bolesti crijeva; bolesti i poremećaja dišnog sustava i dišnih puteva, alergijskog rinitisa, astme i reaktivnih bolesti dišnih puteva i kronične opstruktivne plućne bolesti; bolesti i poremećaja koji su posredovani ili rezultiraju sa upalom, artritisom, reumatoidnim artritisom i osteoartritisom, infarktom miokarda, raznih autoimunih bolesti i poremećaja, uveitisa i ateroskleroze, svrbeža/pruritusa, psorijaze; pretilosti; lipidnih poremećaja; raka; krvnog tlaka; stanja ozljeda leđne moždine koja proizlaze iz ili se odnose na disfunkciju imuniteta; te bubrežnih poremećaja.
32. Spoj za uporabu u postupku prema zahtjevu 31, naznačen time da bol je visceralna bol.
33. Spoj za uporabu u postupku prema zahtjevu 32, naznačen time da je visceralna bol povezana sa gastroezofagealnom refluksnom bolesti, sindromom iritabilnog crijeva, upalnom bolesti crijeva, pankreatitisom, ginekološkim ili urološkim poremećajima.
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PCT/US2008/004208 WO2008130481A1 (en) | 2007-04-17 | 2008-03-31 | 2-cyanophenyl fused heterocyclic compounds, and compositions and uses thereof |
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US (2) | US8076345B2 (hr) |
EP (1) | EP2139334B1 (hr) |
JP (1) | JP5498374B2 (hr) |
CN (1) | CN101677569B (hr) |
CA (1) | CA2682692A1 (hr) |
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ES (1) | ES2427999T3 (hr) |
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PL (1) | PL2139334T3 (hr) |
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ES2557281T3 (es) | 2008-02-29 | 2016-01-25 | Evotec Ag | Compuestos amida, composiciones y usos de los mismos |
WO2010066629A2 (en) * | 2008-12-09 | 2010-06-17 | F. Hoffmann-La Roche Ag | Novel azaindoles |
AU2014253493B2 (en) * | 2010-07-06 | 2016-04-14 | Novartis Ag | Tetrahydro-pyrido-pyrimidine derivatives |
UA112517C2 (uk) | 2010-07-06 | 2016-09-26 | Новартіс Аг | Тетрагідропіридопіримідинові похідні |
KR20140025530A (ko) * | 2011-06-27 | 2014-03-04 | 노파르티스 아게 | 테트라히드로-피리도-피리미딘 유도체의 고체 형태 및 염 |
AU2012354094C1 (en) | 2011-12-15 | 2015-10-15 | Novartis Ag | Use of inhibitors of the activity or function of PI3K |
CN103497149A (zh) * | 2013-10-08 | 2014-01-08 | 南京复兴生物科技有限公司 | 一种5-氨甲基吡啶衍生物的制备方法 |
US10183937B2 (en) | 2014-12-09 | 2019-01-22 | Bayer Aktiengesellschaft | 1,3-thiazol-2-yl substituted benzamides |
PT3230281T (pt) | 2014-12-09 | 2021-08-19 | Bayer Ag | Benzamidas substituídas por 1,3-tiazol-2-ilo |
WO2017049498A1 (zh) * | 2015-09-23 | 2017-03-30 | 前湾医药科技(深圳)有限公司 | 一种咪唑并吡啶类化合物与在制备pi3k抑制剂中的应用 |
US20230096028A1 (en) * | 2019-03-01 | 2023-03-30 | Revolution Medicines, Inc. | Bicyclic heterocyclyl compounds and uses thereof |
PE20220934A1 (es) | 2019-05-31 | 2022-05-31 | Chiesi Farm Spa | Derivados de aminoquinazolina como inhibidores del purinoreceptor 3 de p2x (p2x3) |
JP2022534434A (ja) | 2019-05-31 | 2022-07-29 | キエシ・フアルマチエウテイチ・ソチエタ・ペル・アチオニ | P2x3阻害剤としてのピリドピリミジン誘導体 |
WO2022028506A1 (zh) * | 2020-08-06 | 2022-02-10 | 北京泰德制药股份有限公司 | Sos1抑制剂、包含其的药物组合物及其用途 |
CA3196335A1 (en) | 2020-11-27 | 2022-06-02 | Chiesi Farmaceutici S.P.A. | Phthalazine derivatives as p2x3 inhibitors |
EP4251620A1 (en) | 2020-11-27 | 2023-10-04 | Chiesi Farmaceutici S.p.A. | Amino quinazoline derivatives as p2x3 inhibitors |
EP4251617A1 (en) | 2020-11-27 | 2023-10-04 | Chiesi Farmaceutici S.p.A. | (aza)quinoline 4-amines derivatives as p2x3 inhibitors |
US11993580B1 (en) | 2022-12-02 | 2024-05-28 | Neumora Therapeutics, Inc. | Methods of treating neurological disorders |
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2008
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- 2008-03-31 PT PT87424305T patent/PT2139334E/pt unknown
- 2008-03-31 CN CN200880016706.XA patent/CN101677569B/zh not_active Expired - Fee Related
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- 2008-03-31 WO PCT/US2008/004208 patent/WO2008130481A1/en active Search and Examination
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CA2682692A1 (en) | 2008-10-30 |
US20080275037A1 (en) | 2008-11-06 |
ES2427999T3 (es) | 2013-11-05 |
CN101677569B (zh) | 2014-01-22 |
US20120149700A1 (en) | 2012-06-14 |
JP2010524930A (ja) | 2010-07-22 |
CY1114382T1 (el) | 2016-08-31 |
EP2139334B1 (en) | 2013-07-03 |
JP5498374B2 (ja) | 2014-05-21 |
PT2139334E (pt) | 2013-10-02 |
DK2139334T3 (da) | 2013-09-23 |
EP2139334A1 (en) | 2010-01-06 |
WO2008130481A1 (en) | 2008-10-30 |
PL2139334T3 (pl) | 2013-11-29 |
CN101677569A (zh) | 2010-03-24 |
EP2139334A4 (en) | 2011-06-22 |
US8076345B2 (en) | 2011-12-13 |
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