JP2009513575A5 - - Google Patents
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- JP2009513575A5 JP2009513575A5 JP2008534486A JP2008534486A JP2009513575A5 JP 2009513575 A5 JP2009513575 A5 JP 2009513575A5 JP 2008534486 A JP2008534486 A JP 2008534486A JP 2008534486 A JP2008534486 A JP 2008534486A JP 2009513575 A5 JP2009513575 A5 JP 2009513575A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- fluoro
- imidazol
- pyrimidin
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 45
- 125000000623 heterocyclic group Chemical group 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- 239000001257 hydrogen Substances 0.000 claims 31
- -1 hydrogen radicals Chemical group 0.000 claims 30
- 125000005843 halogen group Chemical group 0.000 claims 21
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000004429 atom Chemical group 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 208000010877 cognitive disease Diseases 0.000 claims 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 206010012289 Dementia Diseases 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 239000012458 free base Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000006999 cognitive decline Effects 0.000 claims 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- VGSQFKCYTNOWJM-UHFFFAOYSA-N (2,6-dimethylmorpholin-4-yl)-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]methanone;hydrochloride Chemical compound Cl.C1C(C)OC(C)CN1C(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 VGSQFKCYTNOWJM-UHFFFAOYSA-N 0.000 claims 1
- JUHQUEWVIIDBNH-UHFFFAOYSA-N (3,3-difluoroazetidin-1-yl)-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]methanone;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C(=O)N1CC(F)(F)C1 JUHQUEWVIIDBNH-UHFFFAOYSA-N 0.000 claims 1
- UHDXDZQXNNJWDY-UHFFFAOYSA-N (3,3-difluoropyrrolidin-1-yl)-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]methanone;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C(=O)N1CCC(F)(F)C1 UHDXDZQXNNJWDY-UHFFFAOYSA-N 0.000 claims 1
- AUDGHHREDWBFOE-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]methanone;hydrochloride Chemical compound Cl.C1CN(CC)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 AUDGHHREDWBFOE-UHFFFAOYSA-N 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- DNLNSPKWMVGBHG-UHFFFAOYSA-N 2-amino-N-[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]-N-(oxan-4-yl)benzamide hydrochloride Chemical compound Cl.NC1=C(C(=O)N(C2CCOCC2)C2=NC=C(C(=N2)C=2N(C(=NC2)C)C2CCOCC2)F)C=CC=C1 DNLNSPKWMVGBHG-UHFFFAOYSA-N 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- ADLMNARJRRPSOT-UHFFFAOYSA-N 3-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]benzonitrile;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=CC(C#N)=C1 ADLMNARJRRPSOT-UHFFFAOYSA-N 0.000 claims 1
- QLNHZJLXRCTCMN-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(4-methylsulfonylphenyl)pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(N=1)=CC=NC=1NC1=CC=C(S(C)(=O)=O)C=C1 QLNHZJLXRCTCMN-UHFFFAOYSA-N 0.000 claims 1
- HYESJXMPFNNNAW-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(4-morpholin-4-ylsulfonylphenyl)pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(N=1)=CC=NC=1NC(C=C1)=CC=C1S(=O)(=O)N1CCOCC1 HYESJXMPFNNNAW-UHFFFAOYSA-N 0.000 claims 1
- XHOMOFSUGNNYMU-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(4-pyrrolidin-1-ylsulfonylphenyl)pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(N=1)=CC=NC=1NC(C=C1)=CC=C1S(=O)(=O)N1CCCC1 XHOMOFSUGNNYMU-UHFFFAOYSA-N 0.000 claims 1
- KJJXNFGGNQIJRQ-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[3-(4-methylpiperazin-1-yl)sulfonylphenyl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=CC(NC=2N=C(C=CN=2)C=2N(C(C)=NC=2)C2CCOCC2)=C1 KJJXNFGGNQIJRQ-UHFFFAOYSA-N 0.000 claims 1
- WDBIOFPEYDNNET-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=CC(C=2N(C(C)=NC=2)C2CCOCC2)=N1 WDBIOFPEYDNNET-UHFFFAOYSA-N 0.000 claims 1
- BWNKOIBHTVEFEQ-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-(4-propan-2-ylpiperazin-1-yl)sulfonylphenyl]pyrimidin-2-amine Chemical compound C1CN(C(C)C)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=CC(C=2N(C(C)=NC=2)C2CCOCC2)=N1 BWNKOIBHTVEFEQ-UHFFFAOYSA-N 0.000 claims 1
- HDLRWDBVGGDOBV-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(N=1)=CC=NC=1NC(C=C1)=CC=C1CN1CCOCC1 HDLRWDBVGGDOBV-UHFFFAOYSA-N 0.000 claims 1
- CIUVREIHECGYBX-UHFFFAOYSA-N 4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 CIUVREIHECGYBX-UHFFFAOYSA-N 0.000 claims 1
- BDXZIUJTKUIELX-UHFFFAOYSA-N 4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]benzonitrile;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(C#N)C=C1 BDXZIUJTKUIELX-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- BLFWGFFZXXRNOQ-UHFFFAOYSA-N 5-[5-fluoro-2-[4-(4-methylpiperazin-1-yl)sulfonylanilino]pyrimidin-4-yl]-1-(oxan-4-yl)imidazole-2-carbonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C#N)=NC=2)C2CCOCC2)=N1 BLFWGFFZXXRNOQ-UHFFFAOYSA-N 0.000 claims 1
- HOKUVVAWNADSQH-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(3-methylsulfonylphenyl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=CC(S(C)(=O)=O)=C1 HOKUVVAWNADSQH-UHFFFAOYSA-N 0.000 claims 1
- JHVNKPANIZNDOB-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(4-methylsulfonylphenyl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(S(C)(=O)=O)C=C1 JHVNKPANIZNDOB-UHFFFAOYSA-N 0.000 claims 1
- MCCNGBGRWZAASD-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(4-morpholin-4-ylsulfonylphenyl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1S(=O)(=O)N1CCOCC1 MCCNGBGRWZAASD-UHFFFAOYSA-N 0.000 claims 1
- JFZIVITZPGBERZ-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(4-piperazin-1-ylsulfonylphenyl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1S(=O)(=O)N1CCNCC1 JFZIVITZPGBERZ-UHFFFAOYSA-N 0.000 claims 1
- KVUCXDUGBPIVIY-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(4-propan-2-ylsulfonylphenyl)pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C(C)C)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 KVUCXDUGBPIVIY-UHFFFAOYSA-N 0.000 claims 1
- CUXVJGARBZCZCY-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(4-pyrrolidin-1-ylsulfonylphenyl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1S(=O)(=O)N1CCCC1 CUXVJGARBZCZCY-UHFFFAOYSA-N 0.000 claims 1
- XWUFNANHAZTEFC-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[3-methylsulfonyl-4-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1S(C)(=O)=O)=CC=C1CN1CCOCC1 XWUFNANHAZTEFC-UHFFFAOYSA-N 0.000 claims 1
- BMCLFHVOOIZFNK-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-(1-morpholin-4-ylethyl)phenyl]pyrimidin-2-amine Chemical compound C=1C=C(NC=2N=C(C(F)=CN=2)C=2N(C(C)=NC=2)C2CCOCC2)C=CC=1C(C)N1CCOCC1 BMCLFHVOOIZFNK-UHFFFAOYSA-N 0.000 claims 1
- UTFUIZWRDLATQF-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-(2-morpholin-4-ylethyl)phenyl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1CCN1CCOCC1 UTFUIZWRDLATQF-UHFFFAOYSA-N 0.000 claims 1
- FMEORCWNFFMXER-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-(4-methylpiperazin-1-yl)sulfonyl-3-(trifluoromethoxy)phenyl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C(C(=C1)OC(F)(F)F)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 FMEORCWNFFMXER-UHFFFAOYSA-N 0.000 claims 1
- OTGRAAUTGFNVIC-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 OTGRAAUTGFNVIC-UHFFFAOYSA-N 0.000 claims 1
- PEYBMQWFUHAKRT-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1CN1CCOCC1 PEYBMQWFUHAKRT-UHFFFAOYSA-N 0.000 claims 1
- HPWNIPMSABCNAE-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-(oxan-2-ylmethylsulfonyl)phenyl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1S(=O)(=O)CC1CCCCO1 HPWNIPMSABCNAE-UHFFFAOYSA-N 0.000 claims 1
- BCPCWRAHMRSSBP-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-(trifluoromethyl)phenyl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(C(F)(F)F)C=C1 BCPCWRAHMRSSBP-UHFFFAOYSA-N 0.000 claims 1
- ZCNYDSWSOIKGPQ-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(S(C)(=O)=O)C(C(F)(F)F)=C1 ZCNYDSWSOIKGPQ-UHFFFAOYSA-N 0.000 claims 1
- IOLWECNTCVXLQV-UHFFFAOYSA-N 5-fluoro-4-[3-methyl-2-(trifluoromethyl)imidazol-4-yl]-n-[4-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.N1=C(C(F)(F)F)N(C)C(C=2C(=CN=C(NC=3C=CC(CN4CCOCC4)=CC=3)N=2)F)=C1 IOLWECNTCVXLQV-UHFFFAOYSA-N 0.000 claims 1
- MVSNVAGWRVEZEP-UHFFFAOYSA-N 5-fluoro-n-[3-methyl-4-(4-methylpiperazin-1-yl)sulfonylphenyl]-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1S(=O)(=O)C(C(=C1)C)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 MVSNVAGWRVEZEP-UHFFFAOYSA-N 0.000 claims 1
- ZWOFTMCYCCXBPH-UHFFFAOYSA-N 5-fluoro-n-[4-(2-methoxyethylsulfonyl)phenyl]-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)CCOC)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 ZWOFTMCYCCXBPH-UHFFFAOYSA-N 0.000 claims 1
- TVBCVACLARFLNB-UHFFFAOYSA-N 5-fluoro-n-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-4-[3-(oxan-4-yl)-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(=NC=2)C(F)(F)F)C2CCOCC2)=N1 TVBCVACLARFLNB-UHFFFAOYSA-N 0.000 claims 1
- KWPKLLKLLVEXEJ-UHFFFAOYSA-N 5-fluoro-n-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-4-[3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C=NC=2)C2CCOCC2)=N1 KWPKLLKLLVEXEJ-UHFFFAOYSA-N 0.000 claims 1
- NVAHGLXBXBUJLJ-MRXNPFEDSA-N 5-fluoro-n-[4-[(3r)-3-methylmorpholin-4-yl]sulfonylphenyl]-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C[C@@H]1COCCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 NVAHGLXBXBUJLJ-MRXNPFEDSA-N 0.000 claims 1
- ITIVWLXGVTYUJH-PMACEKPBSA-N 5-fluoro-n-[4-[[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]phenyl]-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2S(=O)(=O)C(C=C1)=CC=C1NC(N=1)=NC=C(F)C=1C1=CN=C(C)N1C1CCOCC1 ITIVWLXGVTYUJH-PMACEKPBSA-N 0.000 claims 1
- OQKLTFPVRPDGRN-UHFFFAOYSA-N 6-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-1,1-dioxo-2,3-dihydrothiochromen-4-one;hydrochloride Chemical compound Cl.CC1=NC=C(C=2C(=CN=C(NC=3C=C4C(S(CCC4=O)(=O)=O)=CC=3)N=2)F)N1C1CCOCC1 OQKLTFPVRPDGRN-UHFFFAOYSA-N 0.000 claims 1
- LDARYERYIPQHMP-UHFFFAOYSA-N 6-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-1,1-dioxo-3,4-dihydro-2h-thiochromen-4-ol;hydrochloride Chemical compound Cl.CC1=NC=C(C=2C(=CN=C(NC=3C=C4C(S(CCC4O)(=O)=O)=CC=3)N=2)F)N1C1CCOCC1 LDARYERYIPQHMP-UHFFFAOYSA-N 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 208000031091 Amnestic disease Diseases 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- VTWOCPCARMHLSC-UHFFFAOYSA-N Cl.NC1=C(C(=O)N(C)CCO)C=CC=C1 Chemical compound Cl.NC1=C(C(=O)N(C)CCO)C=CC=C1 VTWOCPCARMHLSC-UHFFFAOYSA-N 0.000 claims 1
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000014060 Niemann-Pick disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010034010 Parkinsonism Diseases 0.000 claims 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
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| WO2010009166A1 (en) | 2008-07-14 | 2010-01-21 | Gilead Colorado, Inc. | Oxindolyl inhibitor compounds |
| NZ602832A (en) | 2008-07-14 | 2014-04-30 | Gilead Sciences Inc | Fused heterocyclic hdac inhibitor compounds |
| JP5640005B2 (ja) * | 2008-07-14 | 2014-12-10 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｄａｃおよび／またはｃｄｋ阻害剤としてのイミダゾシルピリジン化合物 |
| JP2011529504A (ja) | 2008-07-28 | 2011-12-08 | ギリアード サイエンシーズ， インコーポレイテッド | シクロアルキリデンヒストン脱アセチル化酵素阻害剤化合物およびヘテロシクロアルキリデンヒストン脱アセチル化酵素阻害剤化合物 |
| US8536185B2 (en) * | 2008-09-22 | 2013-09-17 | Cayman Chemical Company, Incorporated | Multiheteroaryl compounds as inhibitors of H-PGDS and their use for treating prostaglandin D2 mediated diseases |
| JP2012524063A (ja) | 2009-04-15 | 2012-10-11 | アストラゼネカ・アクチエボラーグ | アルツハイマー病などのグリコーゲンシンターゼキナーゼ３関連障害の治療に有用なイミダゾール置換ピリミジン |
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| WO2010144378A2 (en) | 2009-06-08 | 2010-12-16 | Gilead Colorado, Inc. | Cycloalkylcarbamate benzamide aniline hdac inhibitor compounds |
| KR20120031170A (ko) | 2009-06-08 | 2012-03-30 | 길리애드 사이언시즈, 인코포레이티드 | 알카노일아미노 벤즈아미드 아닐린 ｈｄａｃ 저해제 화합물 |
| WO2012050517A1 (en) * | 2010-10-14 | 2012-04-19 | Astrazeneca Ab | Imidazole substituted pyrimidine having a high gsk3 inhibiting potency as well as pan-kinase selectivity |
| CZ305457B6 (cs) | 2011-02-28 | 2015-09-30 | Ústav organické chemie a biochemie, Akademie věd ČR v. v. i. | Pyrimidinové sloučeniny inhibující tvorbu oxidu dusnatého a prostaglandinu E2, způsob výroby a použití |
| JP2017524739A (ja) | 2014-07-17 | 2017-08-31 | アンセルムＩｎｓｅｒｍ | 神経筋接合部関連疾患の処置方法 |
| WO2016207366A1 (en) | 2015-06-26 | 2016-12-29 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of viral infections |
| GB201519573D0 (en) | 2015-11-05 | 2015-12-23 | King S College London | Combination |
| BR112022018477A2 (pt) * | 2020-03-23 | 2022-11-01 | Whan In Pharmaceutical Co Ltd | Composto derivado de pirimidina, composição compreendendo o mesmo, e seus usos na prevenção ou tratamento de doenças neurodegenerativas e câncer |
| KR102342803B1 (ko) * | 2020-03-23 | 2021-12-24 | 환인제약 주식회사 | 신규한 피리미딘 유도체 및 이를 포함하는 신경퇴행성 질환 및 암의 예방 또는 치료용 조성물 |
| TW202227401A (zh) * | 2020-10-23 | 2022-07-16 | 大陸商重慶兩江藥物研發中心有限公司 | 用於持續釋放治療劑的前藥及其用途 |
| CN114426542B (zh) * | 2020-10-29 | 2023-06-30 | 苏州亚宝药物研发有限公司 | 取代的二芳基胺化合物及其药物组合物、制备方法和用途 |
| US20240239774A1 (en) * | 2021-04-28 | 2024-07-18 | Cornell University | Soluble adenylyl cyclase (sac) inhibitors and uses thereof |
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| DE3530710A1 (de) | 1985-08-28 | 1987-03-05 | Hoechst Ag | Verfahren zur herstellung von halogenphenyl-oxethyl-sulfiden und deren oxidationsprodukten |
| GB0021726D0 (en) * | 2000-09-05 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| SE0100569D0 (sv) * | 2001-02-20 | 2001-02-20 | Astrazeneca Ab | New compounds |
| EP1423388B1 (en) * | 2001-02-20 | 2008-12-03 | AstraZeneca AB | 2-arylamino-pyrimidines for the treatment of gsk3-related disorders |
| SE0102439D0 (sv) | 2001-07-05 | 2001-07-05 | Astrazeneca Ab | New compounds |
| MXPA04004178A (es) * | 2001-11-01 | 2004-09-06 | Janssen Pharmaceutica Nv | Heteroarilaminas como inhibidores de glucogeno cintasa cinasa 3beta. |
| GB0205693D0 (en) * | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| US7442697B2 (en) * | 2002-03-09 | 2008-10-28 | Astrazeneca Ab | 4-imidazolyl substituted pyrimidine derivatives with CDK inhibitory activity |
| CA2491895C (en) * | 2002-07-09 | 2011-01-18 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-jun n-terminal kinases (jnk) and other protein kinases |
| GB0226583D0 (en) * | 2002-11-14 | 2002-12-18 | Cyclacel Ltd | Compounds |
| GB0229581D0 (en) * | 2002-12-19 | 2003-01-22 | Cyclacel Ltd | Use |
| JP2006518381A (ja) * | 2003-02-07 | 2006-08-10 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼのインヒビターとして有用なヘテロアリール置換ピロール |
| WO2004083203A1 (en) * | 2003-03-13 | 2004-09-30 | Vertex Pharmaceuticals Incorporated | Compositions useful as protein kinase inhibitors |
| GB0311276D0 (en) * | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| JP2007500178A (ja) * | 2003-07-30 | 2007-01-11 | サイクラセル・リミテッド | プロテインキナーゼ阻害剤としてのピリジニルアミノ−ピリミジン誘導体 |
| TW200528101A (en) * | 2004-02-03 | 2005-09-01 | Astrazeneca Ab | Chemical compounds |
| US7132651B2 (en) | 2004-04-23 | 2006-11-07 | Framatome Anp, Inc. | In-situ BWR and PWR CRUD flake analysis method and tool |
| MX2008001428A (es) * | 2005-07-30 | 2008-04-04 | Astrazeneca Ab | Compuestos de imidazolil-pirimidina para uso en el tratamiento de trastornos proliferativos. |
| TW200815418A (en) * | 2006-06-27 | 2008-04-01 | Astrazeneca Ab | New compounds I |
| JP2012524063A (ja) * | 2009-04-15 | 2012-10-11 | アストラゼネカ・アクチエボラーグ | アルツハイマー病などのグリコーゲンシンターゼキナーゼ３関連障害の治療に有用なイミダゾール置換ピリミジン |
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2006
- 2006-09-29 UY UY29827A patent/UY29827A1/es not_active Application Discontinuation
- 2006-09-29 AR ARP060104310A patent/AR058073A1/es not_active Application Discontinuation
- 2006-10-02 US US12/089,008 patent/US20090105252A1/en not_active Abandoned
- 2006-10-02 RU RU2008110910/04A patent/RU2433128C2/ru not_active IP Right Cessation
- 2006-10-02 UA UAA200802783A patent/UA92181C2/ru unknown
- 2006-10-02 BR BRPI0616658-0A patent/BRPI0616658A2/pt not_active IP Right Cessation
- 2006-10-02 SG SG201007265-0A patent/SG166125A1/en unknown
- 2006-10-02 WO PCT/SE2006/001116 patent/WO2007040440A1/en not_active Ceased
- 2006-10-02 AU AU2006297890A patent/AU2006297890B2/en not_active Ceased
- 2006-10-02 CA CA002624875A patent/CA2624875A1/en not_active Abandoned
- 2006-10-02 KR KR1020087010755A patent/KR20080059423A/ko not_active Ceased
- 2006-10-02 NZ NZ591316A patent/NZ591316A/en not_active IP Right Cessation
- 2006-10-02 CN CNA2006800454648A patent/CN101326179A/zh active Pending
- 2006-10-02 JP JP2008534486A patent/JP2009513575A/ja active Pending
- 2006-10-02 EP EP06799716A patent/EP1945628A4/en not_active Withdrawn
- 2006-10-02 NZ NZ566804A patent/NZ566804A/en not_active IP Right Cessation
- 2006-10-03 TW TW095136796A patent/TW200800957A/zh unknown
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2008
- 2008-03-13 IL IL190150A patent/IL190150A0/en not_active IP Right Cessation
- 2008-04-02 ZA ZA200802897A patent/ZA200802897B/xx unknown
- 2008-04-28 EC EC2008008405A patent/ECSP088405A/es unknown
- 2008-04-30 NO NO20082067A patent/NO20082067L/no not_active Application Discontinuation
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2011
- 2011-03-03 AU AU2011200948A patent/AU2011200948A1/en not_active Abandoned
- 2011-04-20 RU RU2011115406/04A patent/RU2011115406A/ru not_active Application Discontinuation
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