JP2013526560A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013526560A5 JP2013526560A5 JP2013510619A JP2013510619A JP2013526560A5 JP 2013526560 A5 JP2013526560 A5 JP 2013526560A5 JP 2013510619 A JP2013510619 A JP 2013510619A JP 2013510619 A JP2013510619 A JP 2013510619A JP 2013526560 A5 JP2013526560 A5 JP 2013526560A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- dioxo
- quinazolin
- trifluoromethyl
- pyrazol
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims 71
- 229910052736 halogen Inorganic materials 0.000 claims 53
- -1 phenyloxycarbonyl Chemical group 0.000 claims 46
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 43
- 229910052799 carbon Inorganic materials 0.000 claims 36
- 125000004432 carbon atom Chemical group C* 0.000 claims 34
- 150000002367 halogens Chemical class 0.000 claims 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 34
- 125000004430 oxygen atom Chemical group O* 0.000 claims 34
- 125000002947 alkylene group Chemical group 0.000 claims 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 27
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 27
- 125000005843 halogen group Chemical group 0.000 claims 20
- 150000001408 amides Chemical class 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 14
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 14
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 13
- 125000001188 haloalkyl group Chemical group 0.000 claims 13
- 125000004429 atom Chemical group 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 239000001301 oxygen Substances 0.000 claims 8
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 4
- IVVLIZMRBQDOKH-UHFFFAOYSA-N 2,4-dioxo-1h-quinazoline-3-sulfonamide Chemical class C1=CC=C2C(=O)N(S(=O)(=O)N)C(=O)NC2=C1 IVVLIZMRBQDOKH-UHFFFAOYSA-N 0.000 claims 4
- 102000003678 AMPA Receptors Human genes 0.000 claims 4
- 108090000078 AMPA Receptors Proteins 0.000 claims 4
- 102000000079 Kainic Acid Receptors Human genes 0.000 claims 4
- 108010069902 Kainic Acid Receptors Proteins 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 4
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 229910052717 sulfur Chemical group 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 150000003839 salts Chemical group 0.000 claims 3
- NDUJLZBXMNTSBL-UHFFFAOYSA-N 2-methylpropyl n-[6-(2-methylimidazol-1-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCC(C)C)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CN=C1C NDUJLZBXMNTSBL-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- MLAGKSQNSIDZON-UHFFFAOYSA-N ethyl 4-[[6-imidazol-1-yl-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-methylsulfonylamino]-4-oxobutanoate Chemical compound C1=C2C(=O)N(N(C(=O)CCC(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CN=C1 MLAGKSQNSIDZON-UHFFFAOYSA-N 0.000 claims 2
- JLIWMWNRPMAQDE-UHFFFAOYSA-N ethyl n-[2,4-dioxo-6-pyrrol-1-yl-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CC=C1 JLIWMWNRPMAQDE-UHFFFAOYSA-N 0.000 claims 2
- LZKKFWMWYLCMIR-UHFFFAOYSA-N ethyl n-[6-(2-methylimidazol-1-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CN=C1C LZKKFWMWYLCMIR-UHFFFAOYSA-N 0.000 claims 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- GHAOTXAHKLPOHY-UHFFFAOYSA-N methyl n-[2,4-dioxo-6-pyrrol-1-yl-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CC=C1 GHAOTXAHKLPOHY-UHFFFAOYSA-N 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- UBGSGEQFLYYDHJ-UHFFFAOYSA-N n-[2,4-dioxo-6-(1,2,4-triazol-4-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-3-methyl-n-methylsulfonylbutanamide Chemical compound C1=C2C(=O)N(N(C(=O)CC(C)C)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=NN=C1 UBGSGEQFLYYDHJ-UHFFFAOYSA-N 0.000 claims 2
- YVCCSIJIAZCIDI-UHFFFAOYSA-N n-[2,4-dioxo-6-(1,2,4-triazol-4-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylbutanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=NN=C1 YVCCSIJIAZCIDI-UHFFFAOYSA-N 0.000 claims 2
- JEGLVKBRQNUMPV-UHFFFAOYSA-N n-[2,4-dioxo-6-(1,2,4-triazol-4-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylhexanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=NN=C1 JEGLVKBRQNUMPV-UHFFFAOYSA-N 0.000 claims 2
- OZMGZOBSHMRYQD-UHFFFAOYSA-N n-[2,4-dioxo-6-(1,2,4-triazol-4-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpentanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=NN=C1 OZMGZOBSHMRYQD-UHFFFAOYSA-N 0.000 claims 2
- HTZLMKWLBNZVIA-UHFFFAOYSA-N n-[2,4-dioxo-6-pyrrol-1-yl-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylbutanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CC=C1 HTZLMKWLBNZVIA-UHFFFAOYSA-N 0.000 claims 2
- PPGNJVQIQJMQHB-UHFFFAOYSA-N n-[2,4-dioxo-6-pyrrol-1-yl-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpropanamide Chemical compound C1=C2C(=O)N(N(C(=O)CC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CC=C1 PPGNJVQIQJMQHB-UHFFFAOYSA-N 0.000 claims 2
- BOMOYIPXKSPNAP-UHFFFAOYSA-N n-[6-(1-hydroxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-2-methyl-n-methylsulfonylpropanamide Chemical compound N1C(=O)N(N(C(=O)C(C)C)S(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(O)CC)=C2 BOMOYIPXKSPNAP-UHFFFAOYSA-N 0.000 claims 2
- XJELTUDQERWLNA-UHFFFAOYSA-N n-[6-(1-hydroxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylbutanamide Chemical compound FC(F)(F)C1=C(C(O)CC)C=C2C(=O)N(N(C(=O)CCC)S(C)(=O)=O)C(=O)NC2=C1 XJELTUDQERWLNA-UHFFFAOYSA-N 0.000 claims 2
- YEDSGMDPSBCYNX-UHFFFAOYSA-N n-[6-(1-hydroxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylhexanamide Chemical compound FC(F)(F)C1=C(C(O)CC)C=C2C(=O)N(N(C(=O)CCCCC)S(C)(=O)=O)C(=O)NC2=C1 YEDSGMDPSBCYNX-UHFFFAOYSA-N 0.000 claims 2
- QJKQFGAWBHENDY-UHFFFAOYSA-N n-[6-(1-hydroxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpentanamide Chemical compound FC(F)(F)C1=C(C(O)CC)C=C2C(=O)N(N(C(=O)CCCC)S(C)(=O)=O)C(=O)NC2=C1 QJKQFGAWBHENDY-UHFFFAOYSA-N 0.000 claims 2
- YPKAOLRNKVTYFI-UHFFFAOYSA-N n-[6-imidazol-1-yl-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-2-methyl-n-methylsulfonylpropanamide Chemical compound C1=C2C(=O)N(N(C(=O)C(C)C)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CN=C1 YPKAOLRNKVTYFI-UHFFFAOYSA-N 0.000 claims 2
- GNGHUMJAKNMHJF-UHFFFAOYSA-N n-[6-imidazol-1-yl-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylacetamide Chemical compound C1=C2C(=O)N(N(C(=O)C)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CN=C1 GNGHUMJAKNMHJF-UHFFFAOYSA-N 0.000 claims 2
- JOBQVACFPZZSDL-UHFFFAOYSA-N n-[6-imidazol-1-yl-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylbutanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CN=C1 JOBQVACFPZZSDL-UHFFFAOYSA-N 0.000 claims 2
- XQBGKCCVAQVPMJ-UHFFFAOYSA-N n-[6-imidazol-1-yl-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcyclopentanecarboxamide Chemical compound O=C1NC2=CC(C(F)(F)F)=C(N3C=NC=C3)C=C2C(=O)N1N(S(=O)(=O)C)C(=O)C1CCCC1 XQBGKCCVAQVPMJ-UHFFFAOYSA-N 0.000 claims 2
- TYCKWFSSVSUSGF-UHFFFAOYSA-N n-[6-imidazol-1-yl-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylhexanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CN=C1 TYCKWFSSVSUSGF-UHFFFAOYSA-N 0.000 claims 2
- ZLYBEOITZOYBNU-UHFFFAOYSA-N n-[6-imidazol-1-yl-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpentanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CN=C1 ZLYBEOITZOYBNU-UHFFFAOYSA-N 0.000 claims 2
- IQIZJOQEZOXGHG-UHFFFAOYSA-N n-[6-imidazol-1-yl-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpropanamide Chemical compound C1=C2C(=O)N(N(C(=O)CC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CN=C1 IQIZJOQEZOXGHG-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- DRUVVKLSVGICLA-UHFFFAOYSA-N propyl n-[6-(2-methylimidazol-1-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1N1C=CN=C1C DRUVVKLSVGICLA-UHFFFAOYSA-N 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims 1
- QSUDOXCHJOMXQN-UHFFFAOYSA-N 2,2-dimethyl-n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonylpropanamide Chemical compound CC(C)C1=CC=2NC(=O)N(N(C(=O)C(C)(C)C)S(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C QSUDOXCHJOMXQN-UHFFFAOYSA-N 0.000 claims 1
- LKINLZPGWBCPEA-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]-n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonylacetamide Chemical compound C1=C2C(=O)N(N(C(=O)COCCOCCOC)S(C)(=O)=O)C(=O)NC2=CC(C(C)C)=C1C1=CC=NN1C LKINLZPGWBCPEA-UHFFFAOYSA-N 0.000 claims 1
- IQNLEZUUOZOODO-UHFFFAOYSA-N 2-methoxyethyl n-[2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCOC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C(C)C IQNLEZUUOZOODO-UHFFFAOYSA-N 0.000 claims 1
- QULLMZWZLOVUGC-UHFFFAOYSA-N 2-methoxyethyl n-[2,4-dioxo-6-(oxolan-2-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCOC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCO1 QULLMZWZLOVUGC-UHFFFAOYSA-N 0.000 claims 1
- GSNPEZBRUDOAGG-UHFFFAOYSA-N 2-methoxyethyl n-[6-(1-hydroxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound N1C(=O)N(N(C(=O)OCCOC)S(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(O)CC)=C2 GSNPEZBRUDOAGG-UHFFFAOYSA-N 0.000 claims 1
- DBLCUEDMSVGOBZ-UHFFFAOYSA-N 2-methoxyethyl n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound N1C(=O)N(N(C(=O)OCCOC)S(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(OC)CC)=C2 DBLCUEDMSVGOBZ-UHFFFAOYSA-N 0.000 claims 1
- SVBYLOZLJLQEON-UHFFFAOYSA-N 2-methoxyethyl n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCOC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C SVBYLOZLJLQEON-UHFFFAOYSA-N 0.000 claims 1
- LKMNNNOMPMQXLO-UHFFFAOYSA-N 2-methoxyethyl n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCOC)S(C)(=O)=O)C(=O)NC2=CC(C(C)C)=C1C1=CC=NN1C LKMNNNOMPMQXLO-UHFFFAOYSA-N 0.000 claims 1
- XIFUFSYDXGNYQO-UHFFFAOYSA-N 2-methoxyethyl n-[7-(difluoromethyl)-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCOC)S(C)(=O)=O)C(=O)NC2=CC(C(F)F)=C1C1=CC=NN1C(C)C XIFUFSYDXGNYQO-UHFFFAOYSA-N 0.000 claims 1
- LMESZZNAMYFFHU-UHFFFAOYSA-N 2-methoxyethyl n-[7-ethyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound CCC1=CC=2NC(=O)N(N(C(=O)OCCOC)S(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C LMESZZNAMYFFHU-UHFFFAOYSA-N 0.000 claims 1
- DZHZUWMKHWNTJL-UHFFFAOYSA-N 2-methyl-n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpropanamide Chemical compound C1=C2C(=O)N(N(C(=O)C(C)C)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C DZHZUWMKHWNTJL-UHFFFAOYSA-N 0.000 claims 1
- NYSZQPCKHFHFAX-UHFFFAOYSA-N 2-methylpropyl 3-[2-methylpropoxycarbonyl(methylsulfonyl)amino]-6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-ylquinazoline-1-carboxylate Chemical compound C1=C2C(=O)N(N(C(=O)OCC(C)C)S(C)(=O)=O)C(=O)N(C(=O)OCC(C)C)C2=CC(C(C)C)=C1C1=CC=NN1C NYSZQPCKHFHFAX-UHFFFAOYSA-N 0.000 claims 1
- RWYTYHKQBQBGSO-UHFFFAOYSA-N 2-methylpropyl n-[2,4-dioxo-6-(oxolan-2-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCC(C)C)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCO1 RWYTYHKQBQBGSO-UHFFFAOYSA-N 0.000 claims 1
- PYHPSSJHGKGGCL-UHFFFAOYSA-N 2-methylpropyl n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound N1C(=O)N(N(C(=O)OCC(C)C)S(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(OC)CC)=C2 PYHPSSJHGKGGCL-UHFFFAOYSA-N 0.000 claims 1
- HAMGBHISHHOSAX-UHFFFAOYSA-N 2-methylpropyl n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCC(C)C)S(C)(=O)=O)C(=O)NC2=CC(C(C)C)=C1C1=CC=NN1C HAMGBHISHHOSAX-UHFFFAOYSA-N 0.000 claims 1
- WNHMQYSCHYYXEQ-UHFFFAOYSA-N 2-methylpropyl n-[7-ethyl-6-(2-ethylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound CCC1=CC=2NC(=O)N(N(C(=O)OCC(C)C)S(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1CC WNHMQYSCHYYXEQ-UHFFFAOYSA-N 0.000 claims 1
- YZRPCSFIFFFXPK-UHFFFAOYSA-N 2-methylpropyl n-[7-ethyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound CCC1=CC=2NC(=O)N(N(C(=O)OCC(C)C)S(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C YZRPCSFIFFFXPK-UHFFFAOYSA-N 0.000 claims 1
- QDOATPIHYNWLAZ-UHFFFAOYSA-N CCN1C(=CC=N1)C2=C(C=C3C(=C2)C(=O)N(C(=O)N3)C(CCCOC(=O)N)S(=O)(=O)C)C(F)(F)F Chemical compound CCN1C(=CC=N1)C2=C(C=C3C(=C2)C(=O)N(C(=O)N3)C(CCCOC(=O)N)S(=O)(=O)C)C(F)(F)F QDOATPIHYNWLAZ-UHFFFAOYSA-N 0.000 claims 1
- GGQONGCEHSEWMV-UHFFFAOYSA-N [2-[[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-methylsulfonylamino]-2-oxoethyl] acetate Chemical compound CC(C)C1=CC=2NC(=O)N(N(C(=O)COC(C)=O)S(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C GGQONGCEHSEWMV-UHFFFAOYSA-N 0.000 claims 1
- IVDVRPNMFCJHBY-UHFFFAOYSA-N [2-methyl-1-[[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-methylsulfonylamino]-1-oxopropan-2-yl] acetate Chemical compound CC(C)C1=CC=2NC(=O)N(N(C(=O)C(C)(C)OC(C)=O)S(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C IVDVRPNMFCJHBY-UHFFFAOYSA-N 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- NOLRQFQKHXXILL-UHFFFAOYSA-N butyl 3-[butoxycarbonyl(methylsulfonyl)amino]-6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-ylquinazoline-1-carboxylate Chemical compound C1=C2C(=O)N(N(C(=O)OCCCC)S(C)(=O)=O)C(=O)N(C(=O)OCCCC)C2=CC(C(C)C)=C1C1=CC=NN1C NOLRQFQKHXXILL-UHFFFAOYSA-N 0.000 claims 1
- SIZPKNGSAZTSLZ-UHFFFAOYSA-N butyl n-[2,4-dioxo-6-(oxolan-2-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCO1 SIZPKNGSAZTSLZ-UHFFFAOYSA-N 0.000 claims 1
- JVAKPFMENMZQBU-UHFFFAOYSA-N butyl n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound FC(F)(F)C1=C(C(CC)OC)C=C2C(=O)N(N(C(=O)OCCCC)S(C)(=O)=O)C(=O)NC2=C1 JVAKPFMENMZQBU-UHFFFAOYSA-N 0.000 claims 1
- HRLWLWDJZBGEHP-UHFFFAOYSA-N butyl n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCCC)S(C)(=O)=O)C(=O)NC2=CC(C(C)C)=C1C1=CC=NN1C HRLWLWDJZBGEHP-UHFFFAOYSA-N 0.000 claims 1
- KUBBBKLWGZPYEM-UHFFFAOYSA-N butyl n-[7-ethyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCCC)S(C)(=O)=O)C(=O)NC2=CC(CC)=C1C1=CC=NN1C KUBBBKLWGZPYEM-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- CULMQQBMLOHLKX-UHFFFAOYSA-N ethyl 3-[[2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-methylsulfonylamino]-3-oxopropanoate Chemical compound C1=C2C(=O)N(N(C(=O)CC(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C(C)C CULMQQBMLOHLKX-UHFFFAOYSA-N 0.000 claims 1
- NCAIRMGINJNQMR-UHFFFAOYSA-N ethyl 3-[[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-methylsulfonylamino]-3-oxopropanoate Chemical compound C1=C2C(=O)N(N(C(=O)CC(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(C)C)=C1C1=CC=NN1C NCAIRMGINJNQMR-UHFFFAOYSA-N 0.000 claims 1
- NXHNYQSNPLETGT-UHFFFAOYSA-N ethyl 3-[ethoxycarbonyl(methylsulfonyl)amino]-6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-ylquinazoline-1-carboxylate Chemical compound C1=C2C(=O)N(N(C(=O)OCC)S(C)(=O)=O)C(=O)N(C(=O)OCC)C2=CC(C(C)C)=C1C1=CC=NN1C NXHNYQSNPLETGT-UHFFFAOYSA-N 0.000 claims 1
- YDNFQDGVGNMQHV-UHFFFAOYSA-N ethyl 4-[[2,4-dioxo-6-(oxolan-2-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-methylsulfonylamino]-4-oxobutanoate Chemical compound C1=C2C(=O)N(N(C(=O)CCC(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCO1 YDNFQDGVGNMQHV-UHFFFAOYSA-N 0.000 claims 1
- TWRBQQWPWUERCD-UHFFFAOYSA-N ethyl 4-[[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-methylsulfonylamino]-4-oxobutanoate Chemical compound C1=C2C(=O)N(N(C(=O)CCC(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(C)C)=C1C1=CC=NN1C TWRBQQWPWUERCD-UHFFFAOYSA-N 0.000 claims 1
- OQWVUVIUJUMGLC-UHFFFAOYSA-N ethyl 5-[[2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-methylsulfonylamino]-5-oxopentanoate Chemical compound C1=C2C(=O)N(N(C(=O)CCCC(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C(C)C OQWVUVIUJUMGLC-UHFFFAOYSA-N 0.000 claims 1
- MOPHIJLTERBGND-UHFFFAOYSA-N ethyl 5-[[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-methylsulfonylamino]-5-oxopentanoate Chemical compound C1=C2C(=O)N(N(C(=O)CCCC(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(C)C)=C1C1=CC=NN1C MOPHIJLTERBGND-UHFFFAOYSA-N 0.000 claims 1
- IAAUSGCKWTYRJK-UHFFFAOYSA-N ethyl n-[2,4-dioxo-6-(oxolan-2-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCO1 IAAUSGCKWTYRJK-UHFFFAOYSA-N 0.000 claims 1
- HAEYTNLLTNYJPJ-UHFFFAOYSA-N ethyl n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound FC(F)(F)C1=C(C(CC)OC)C=C2C(=O)N(N(C(=O)OCC)S(C)(=O)=O)C(=O)NC2=C1 HAEYTNLLTNYJPJ-UHFFFAOYSA-N 0.000 claims 1
- GRTLZQFECYUHJK-UHFFFAOYSA-N ethyl n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(C)C)=C1C1=CC=NN1C GRTLZQFECYUHJK-UHFFFAOYSA-N 0.000 claims 1
- DDCGLMYADKBOCF-UHFFFAOYSA-N ethyl n-[7-(difluoromethyl)-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)F)=C1C1=CC=NN1C(C)C DDCGLMYADKBOCF-UHFFFAOYSA-N 0.000 claims 1
- LSGABLAFUVROLQ-UHFFFAOYSA-N ethyl n-[7-ethyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCC)S(C)(=O)=O)C(=O)NC2=CC(CC)=C1C1=CC=NN1C LSGABLAFUVROLQ-UHFFFAOYSA-N 0.000 claims 1
- NSHRRMAKLQBBSC-UHFFFAOYSA-N hexyl n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound FC(F)(F)C1=C(C(CC)OC)C=C2C(=O)N(N(C(=O)OCCCCCC)S(C)(=O)=O)C(=O)NC2=C1 NSHRRMAKLQBBSC-UHFFFAOYSA-N 0.000 claims 1
- TVPQNQZBXLUMAZ-UHFFFAOYSA-N hexyl n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCCCCC)S(C)(=O)=O)C(=O)NC2=CC(C(C)C)=C1C1=CC=NN1C TVPQNQZBXLUMAZ-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- WHJITSJLKALAHT-UHFFFAOYSA-N methyl 3-[methoxycarbonyl(methylsulfonyl)amino]-6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-ylquinazoline-1-carboxylate Chemical compound C1=C2C(=O)N(N(C(=O)OC)S(C)(=O)=O)C(=O)N(C(=O)OC)C2=CC(C(C)C)=C1C1=CC=NN1C WHJITSJLKALAHT-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- GHNJYJMNVPIONG-UHFFFAOYSA-N methyl n-[2,4-dioxo-6-(oxolan-2-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCO1 GHNJYJMNVPIONG-UHFFFAOYSA-N 0.000 claims 1
- XKACTVWUFHUWQZ-UHFFFAOYSA-N methyl n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound N1C(=O)N(N(C(=O)OC)S(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(OC)CC)=C2 XKACTVWUFHUWQZ-UHFFFAOYSA-N 0.000 claims 1
- FQQXTYCGHSANEJ-UHFFFAOYSA-N methyl n-[7-ethyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound CCC1=CC=2NC(=O)N(N(C(=O)OC)S(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C FQQXTYCGHSANEJ-UHFFFAOYSA-N 0.000 claims 1
- LDOYTRUOTQLNAR-UHFFFAOYSA-N n-[1-acetyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-ylquinazolin-3-yl]-n-methylsulfonylacetamide Chemical compound CC(C)C1=CC=2N(C(C)=O)C(=O)N(N(C(C)=O)S(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C LDOYTRUOTQLNAR-UHFFFAOYSA-N 0.000 claims 1
- ULJBYFOAPRNCKQ-UHFFFAOYSA-N n-[1-acetyl-7-ethyl-6-(2-methylpyrazol-3-yl)-2,4-dioxoquinazolin-3-yl]-n-methylsulfonylacetamide Chemical compound CCC1=CC=2N(C(C)=O)C(=O)N(N(C(C)=O)S(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C ULJBYFOAPRNCKQ-UHFFFAOYSA-N 0.000 claims 1
- FRZNGIVBORGNAT-UHFFFAOYSA-N n-[1-butanoyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-ylquinazolin-3-yl]-n-methylsulfonylbutanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCC)S(C)(=O)=O)C(=O)N(C(=O)CCC)C2=CC(C(C)C)=C1C1=CC=NN1C FRZNGIVBORGNAT-UHFFFAOYSA-N 0.000 claims 1
- OEQVOVGTZSLJDT-UHFFFAOYSA-N n-[2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-2-methyl-n-methylsulfonylpropanamide Chemical compound C1=C2C(=O)N(N(C(=O)C(C)C)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C(C)C OEQVOVGTZSLJDT-UHFFFAOYSA-N 0.000 claims 1
- CJIUNFLTSAUQBQ-UHFFFAOYSA-N n-[2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-3-methylsulfanyl-n-methylsulfonylpropanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCSC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C(C)C CJIUNFLTSAUQBQ-UHFFFAOYSA-N 0.000 claims 1
- UUTUHHRTYYXPCT-UHFFFAOYSA-N n-[2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylacetamide Chemical compound CC(C)N1N=CC=C1C1=CC(C(N(N(C(C)=O)S(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(F)(F)F UUTUHHRTYYXPCT-UHFFFAOYSA-N 0.000 claims 1
- HIARTFKNVRPSCA-UHFFFAOYSA-N n-[2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylbutanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C(C)C HIARTFKNVRPSCA-UHFFFAOYSA-N 0.000 claims 1
- BMVJOPDCUJZLLF-UHFFFAOYSA-N n-[2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylhexanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C(C)C BMVJOPDCUJZLLF-UHFFFAOYSA-N 0.000 claims 1
- IXNNYWKTKJQTFR-UHFFFAOYSA-N n-[2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpropanamide Chemical compound C1=C2C(=O)N(N(C(=O)CC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C(C)C IXNNYWKTKJQTFR-UHFFFAOYSA-N 0.000 claims 1
- CLTHMZRUDXRWFW-UHFFFAOYSA-N n-[2,4-dioxo-6-(oxolan-2-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylacetamide Chemical compound C1=C2C(=O)N(N(C(=O)C)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCO1 CLTHMZRUDXRWFW-UHFFFAOYSA-N 0.000 claims 1
- CKAQBMUASWFJTM-UHFFFAOYSA-N n-[2,4-dioxo-6-(oxolan-2-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylbutanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCO1 CKAQBMUASWFJTM-UHFFFAOYSA-N 0.000 claims 1
- JSITWNIQEYQPOS-UHFFFAOYSA-N n-[2,4-dioxo-6-(oxolan-2-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylhexanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCO1 JSITWNIQEYQPOS-UHFFFAOYSA-N 0.000 claims 1
- ULONVAVEHPUJCR-UHFFFAOYSA-N n-[2,4-dioxo-6-(oxolan-2-yl)-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpentanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1CCCO1 ULONVAVEHPUJCR-UHFFFAOYSA-N 0.000 claims 1
- DTKYQLLQZOFZHK-UHFFFAOYSA-N n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-2-methyl-n-methylsulfonylpropanamide Chemical compound N1C(=O)N(N(C(=O)C(C)C)S(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(OC)CC)=C2 DTKYQLLQZOFZHK-UHFFFAOYSA-N 0.000 claims 1
- PXPWITPFYLSLQV-UHFFFAOYSA-N n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylacetamide Chemical compound N1C(=O)N(N(C(C)=O)S(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(OC)CC)=C2 PXPWITPFYLSLQV-UHFFFAOYSA-N 0.000 claims 1
- DMKNKELJXLUYFQ-UHFFFAOYSA-N n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylbutanamide Chemical compound FC(F)(F)C1=C(C(CC)OC)C=C2C(=O)N(N(C(=O)CCC)S(C)(=O)=O)C(=O)NC2=C1 DMKNKELJXLUYFQ-UHFFFAOYSA-N 0.000 claims 1
- PKOLEBQDQQCHOX-UHFFFAOYSA-N n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylhexanamide Chemical compound FC(F)(F)C1=C(C(CC)OC)C=C2C(=O)N(N(C(=O)CCCCC)S(C)(=O)=O)C(=O)NC2=C1 PKOLEBQDQQCHOX-UHFFFAOYSA-N 0.000 claims 1
- GPXMVWDIVOLXJG-UHFFFAOYSA-N n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpentanamide Chemical compound FC(F)(F)C1=C(C(CC)OC)C=C2C(=O)N(N(C(=O)CCCC)S(C)(=O)=O)C(=O)NC2=C1 GPXMVWDIVOLXJG-UHFFFAOYSA-N 0.000 claims 1
- HCTJNBXSWAYUKZ-UHFFFAOYSA-N n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpropanamide Chemical compound N1C(=O)N(N(C(=O)CC)S(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(OC)CC)=C2 HCTJNBXSWAYUKZ-UHFFFAOYSA-N 0.000 claims 1
- WXKFLAASZKCMKZ-UHFFFAOYSA-N n-[6-(2-ethylpyrazol-3-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-2,2-dimethyl-n-methylsulfonylpropanamide Chemical compound CCN1N=CC=C1C1=CC(C(N(N(C(=O)C(C)(C)C)S(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(F)(F)F WXKFLAASZKCMKZ-UHFFFAOYSA-N 0.000 claims 1
- SRDUILBISUNGSB-UHFFFAOYSA-N n-[6-(2-ethylpyrazol-3-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpropanamide Chemical compound C1=C2C(=O)N(N(C(=O)CC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1CC SRDUILBISUNGSB-UHFFFAOYSA-N 0.000 claims 1
- WYZVFBNGHVCUKE-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-1-propanoyl-7-propan-2-ylquinazolin-3-yl]-n-methylsulfonylpropanamide Chemical compound C1=C2C(=O)N(N(C(=O)CC)S(C)(=O)=O)C(=O)N(C(=O)CC)C2=CC(C(C)C)=C1C1=CC=NN1C WYZVFBNGHVCUKE-UHFFFAOYSA-N 0.000 claims 1
- MGCJKMAAAPALOR-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylbutanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C MGCJKMAAAPALOR-UHFFFAOYSA-N 0.000 claims 1
- BBEHYVQMBSOUIP-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylhexanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C BBEHYVQMBSOUIP-UHFFFAOYSA-N 0.000 claims 1
- WKMKQEIXCXDJJY-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylpentanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)(F)F)=C1C1=CC=NN1C WKMKQEIXCXDJJY-UHFFFAOYSA-N 0.000 claims 1
- OYKTXVPOYRZUEP-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-3-methylsulfanyl-n-methylsulfonylpropanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCSC)S(C)(=O)=O)C(=O)NC2=CC(C(C)C)=C1C1=CC=NN1C OYKTXVPOYRZUEP-UHFFFAOYSA-N 0.000 claims 1
- VQDUIEAQTPFARJ-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonyl-2-morpholin-4-ylacetamide Chemical compound O=C1C=2C=C(C=3N(N=CC=3)C)C(C(C)C)=CC=2NC(=O)N1N(S(C)(=O)=O)C(=O)CN1CCOCC1 VQDUIEAQTPFARJ-UHFFFAOYSA-N 0.000 claims 1
- RDZBUDVJXKBBPE-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonyl-2-phenylmethoxyacetamide Chemical compound O=C1C=2C=C(C=3N(N=CC=3)C)C(C(C)C)=CC=2NC(=O)N1N(S(C)(=O)=O)C(=O)COCC1=CC=CC=C1 RDZBUDVJXKBBPE-UHFFFAOYSA-N 0.000 claims 1
- PWFWOCNMBDQMHP-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonyl-3-morpholin-4-ylpropanamide Chemical compound O=C1C=2C=C(C=3N(N=CC=3)C)C(C(C)C)=CC=2NC(=O)N1N(S(C)(=O)=O)C(=O)CCN1CCOCC1 PWFWOCNMBDQMHP-UHFFFAOYSA-N 0.000 claims 1
- GIZZODLQKVWGFQ-UHFFFAOYSA-N n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonyl-4-morpholin-4-ylbutanamide Chemical compound O=C1C=2C=C(C=3N(N=CC=3)C)C(C(C)C)=CC=2NC(=O)N1N(S(C)(=O)=O)C(=O)CCCN1CCOCC1 GIZZODLQKVWGFQ-UHFFFAOYSA-N 0.000 claims 1
- ZZGYNNMKZQDZAG-UHFFFAOYSA-N n-[7-(difluoromethyl)-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]-n-methylsulfonylacetamide Chemical compound CC(C)N1N=CC=C1C1=CC(C(N(N(C(C)=O)S(C)(=O)=O)C(=O)N2)=O)=C2C=C1C(F)F ZZGYNNMKZQDZAG-UHFFFAOYSA-N 0.000 claims 1
- OMPHIHAVKMKPAD-UHFFFAOYSA-N n-[7-(difluoromethyl)-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]-n-methylsulfonylbutanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)F)=C1C1=CC=NN1C(C)C OMPHIHAVKMKPAD-UHFFFAOYSA-N 0.000 claims 1
- IMTMIZDGRRJMFQ-UHFFFAOYSA-N n-[7-(difluoromethyl)-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]-n-methylsulfonylpentanamide Chemical compound C1=C2C(=O)N(N(C(=O)CCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)F)=C1C1=CC=NN1C(C)C IMTMIZDGRRJMFQ-UHFFFAOYSA-N 0.000 claims 1
- SXZMIYTUWSVYQI-UHFFFAOYSA-N n-[7-(difluoromethyl)-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]-n-methylsulfonylpropanamide Chemical compound C1=C2C(=O)N(N(C(=O)CC)S(C)(=O)=O)C(=O)NC2=CC(C(F)F)=C1C1=CC=NN1C(C)C SXZMIYTUWSVYQI-UHFFFAOYSA-N 0.000 claims 1
- IVWIPFBYUSDDSU-UHFFFAOYSA-N pentyl n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound FC(F)(F)C1=C(C(CC)OC)C=C2C(=O)N(N(C(=O)OCCCCC)S(C)(=O)=O)C(=O)NC2=C1 IVWIPFBYUSDDSU-UHFFFAOYSA-N 0.000 claims 1
- RKGWTHAEKFGVQY-UHFFFAOYSA-N pentyl n-[7-ethyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCCCC)S(C)(=O)=O)C(=O)NC2=CC(CC)=C1C1=CC=NN1C RKGWTHAEKFGVQY-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- KAXSLYLLDXBKTN-UHFFFAOYSA-N propan-2-yl n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound N1C(=O)N(N(C(=O)OC(C)C)S(C)(=O)=O)C(=O)C2=C1C=C(C(F)(F)F)C(C(OC)CC)=C2 KAXSLYLLDXBKTN-UHFFFAOYSA-N 0.000 claims 1
- RKWJYOUGYRFCFU-UHFFFAOYSA-N propan-2-yl n-[7-ethyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound CCC1=CC=2NC(=O)N(N(C(=O)OC(C)C)S(C)(=O)=O)C(=O)C=2C=C1C1=CC=NN1C RKWJYOUGYRFCFU-UHFFFAOYSA-N 0.000 claims 1
- LWEBHFJTRPUIBS-UHFFFAOYSA-N propyl 6-(2-methylpyrazol-3-yl)-3-[methylsulfonyl(propoxycarbonyl)amino]-2,4-dioxo-7-propan-2-ylquinazoline-1-carboxylate Chemical compound C1=C2C(=O)N(N(C(=O)OCCC)S(C)(=O)=O)C(=O)N(C(=O)OCCC)C2=CC(C(C)C)=C1C1=CC=NN1C LWEBHFJTRPUIBS-UHFFFAOYSA-N 0.000 claims 1
- PWFCFUUOLCWCEM-UHFFFAOYSA-N propyl n-[6-(1-methoxypropyl)-2,4-dioxo-7-(trifluoromethyl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound FC(F)(F)C1=C(C(CC)OC)C=C2C(=O)N(N(C(=O)OCCC)S(C)(=O)=O)C(=O)NC2=C1 PWFCFUUOLCWCEM-UHFFFAOYSA-N 0.000 claims 1
- ITRUVOJVVAYTFK-UHFFFAOYSA-N propyl n-[6-(2-methylpyrazol-3-yl)-2,4-dioxo-7-propan-2-yl-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCC)S(C)(=O)=O)C(=O)NC2=CC(C(C)C)=C1C1=CC=NN1C ITRUVOJVVAYTFK-UHFFFAOYSA-N 0.000 claims 1
- YUORRCNHGNIRRT-UHFFFAOYSA-N propyl n-[7-(difluoromethyl)-2,4-dioxo-6-(2-propan-2-ylpyrazol-3-yl)-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCC)S(C)(=O)=O)C(=O)NC2=CC(C(F)F)=C1C1=CC=NN1C(C)C YUORRCNHGNIRRT-UHFFFAOYSA-N 0.000 claims 1
- CCGCJRWSWWEZJW-UHFFFAOYSA-N propyl n-[7-ethyl-6-(2-methylpyrazol-3-yl)-2,4-dioxo-1h-quinazolin-3-yl]-n-methylsulfonylcarbamate Chemical compound C1=C2C(=O)N(N(C(=O)OCCC)S(C)(=O)=O)C(=O)NC2=CC(CC)=C1C1=CC=NN1C CCGCJRWSWWEZJW-UHFFFAOYSA-N 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34657710P | 2010-05-20 | 2010-05-20 | |
| US61/346,577 | 2010-05-20 | ||
| PCT/EP2011/058068 WO2011144666A1 (en) | 2010-05-20 | 2011-05-18 | 2,4-dioxo-1,4-dihydro-2h-quinazolin-3-yl-sulfonamide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013526560A JP2013526560A (ja) | 2013-06-24 |
| JP2013526560A5 true JP2013526560A5 (cg-RX-API-DMAC7.html) | 2014-07-03 |
Family
ID=44260928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013510619A Pending JP2013526560A (ja) | 2010-05-20 | 2011-05-18 | ２，４−ジオキソ−１，４−ジヒドロ−２ｈ−キナゾリン−３−イル−スルホンアミド誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20130053381A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2571865A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2013526560A (cg-RX-API-DMAC7.html) |
| CN (1) | CN102906085A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011144666A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118355020A (zh) * | 2021-12-03 | 2024-07-16 | 吉利德科学公司 | Hiv病毒感染的治疗性化合物 |
| KR20240113832A (ko) | 2021-12-03 | 2024-07-23 | 길리애드 사이언시즈, 인코포레이티드 | Hiv 바이러스 감염 치료용 화합물 |
| CN115414357B (zh) * | 2022-08-30 | 2023-09-22 | 天津医科大学眼科医院 | 一种酰胺类化合物在制备防治近视的药物中的应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9400680D0 (en) | 1994-01-14 | 1994-03-09 | Sandoz Ltd | Improvements in or relating to organic compounds |
| MY132385A (en) | 1995-08-31 | 2007-10-31 | Novartis Ag | 2,3-dioxo-1,2,3,4-tetrahydro-quinoxalinyl derivatives |
| JP2007524596A (ja) | 2003-02-28 | 2007-08-30 | トランスフォーム・ファーマシューティカルズ・インコーポレイテッド | 共結晶医薬組成物 |
| JP4738333B2 (ja) * | 2003-07-09 | 2011-08-03 | パラテック ファーマシューティカルズ インコーポレイテッド | ９−アミノメチルテトラサイクリン化合物のプロドラッグ |
| GB0416730D0 (en) | 2004-07-27 | 2004-09-01 | Novartis Ag | Organic compounds |
| GB0507298D0 (en) * | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
-
2011
- 2011-05-18 JP JP2013510619A patent/JP2013526560A/ja active Pending
- 2011-05-18 CN CN2011800249625A patent/CN102906085A/zh active Pending
- 2011-05-18 EP EP11719840A patent/EP2571865A1/en not_active Withdrawn
- 2011-05-18 WO PCT/EP2011/058068 patent/WO2011144666A1/en not_active Ceased
- 2011-05-18 US US13/638,082 patent/US20130053381A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013516395A5 (cg-RX-API-DMAC7.html) | ||
| RU2492167C2 (ru) | Производные аминотриазола в качестве агонистов alх | |
| CA2565813A1 (en) | Substituted methyl aryl or heteroaryl amide compounds | |
| AR082458A1 (es) | Combinacion que comprende un farmaco antipsicotico y un agonista de taar1 | |
| JP2002540155A5 (cg-RX-API-DMAC7.html) | ||
| RU2009126624A (ru) | Производные 2-(пиперидин-4-ил)-4-фенокси-или фенилаинопиримидина в качестве ненуклеозидных ингибитров обратной транскриптазы | |
| PE20120775A1 (es) | Derivados de tienopirimidindiona como moduladores de trpa1 | |
| RU2017120217A (ru) | 2-амино-5,5-дифтор-6-(фторметил)-6-фенил-3,4,5,6-тетрагидпропиридины в качестве ингибиторов bace1 | |
| RU2009133259A (ru) | Производные пиразола в качестве ингибиторов 11-бета-hsd1 | |
| RU2004127925A (ru) | N3-алкилированные бензимидазольные производные в качестве ингибиторов мек | |
| JP2007514003A5 (cg-RX-API-DMAC7.html) | ||
| RU2001129155A (ru) | Соединения с арильными заместителями (варианты), фармацевтическая композиция и способ лечения расстройства, чувствительного к блокаде натриевых каналов у млекопитающего, способ лечения, профилактики различных заболеваний или уменьшения интенсивности гибели или потери нейронов (варианты), способ облегчения или предупреждения эпилептических припадков у животного (варианты), соединение - радиоактивный лиганд для участка связывания в натриевом канале | |
| CA2361057A1 (en) | Quinoline derivatives and quinazoline derivatives | |
| RU2017116197A (ru) | 2-амино-3,5-дифтор-3,6-диметил-6-фенил-3,4,5,6-тетрагидропиридины как ингибиторы васе1 для лечения болезни альцгеймера | |
| RU2012132692A (ru) | Новые ингибиторы s-нитрозоглутатионредуктазы | |
| WO2012048181A4 (en) | Novel substituted quinoline compounds as s-nitrosoglutathione reductase inhibitors | |
| NZ724602A (en) | Ror-gamma modulators and uses thereof | |
| RU2017116196A (ru) | 2-амино-6-(дифторметил)-5,5-дифтор-6-фенил-3,4,5,6-тетрагидропиридины как ингибиторы васе1 | |
| NZ612544A (en) | Heterocyclic compounds suitable for the treatment of dyslipidemia | |
| RU2016133626A (ru) | 2-амино-3,5,5-трифтор-3,4,5,6-тетрагидропиридины в качестве ингибиторов bace1 для лечения болезни альцгеймера | |
| RU2013132930A (ru) | Производное пиразола | |
| RU2013130879A (ru) | Производные оксазолилметилового эфира в качестве агонистов рецептора alx | |
| JP2012515788A5 (cg-RX-API-DMAC7.html) | ||
| RU2435760C2 (ru) | 1н-хиназолин-2,4-дионы | |
| RU2015117647A (ru) | Новые производные пиразола |