JP2013526560A5

JP2013526560A5 -

Download PDF

Info

Publication number: JP2013526560A5
Authority: JP; Japan
Prior art keywords: dihydro; dioxo; quinazolin; trifluoromethyl; pyrazol
Prior art date: 2011-05-18
Legal status : Pending

Application number

JP2013510619A

Other languages

English (en)

Japanese (ja)

Other versions

JP2013526560A (ja

Filing date

2011-05-18

Publication date

2014-07-03

2011-05-18 Application filed filed Critical

2011-05-18 Priority claimed from PCT/EP2011/058068 external-priority patent/WO2011144666A1/en

2013-06-24 Publication of JP2013526560A publication Critical patent/JP2013526560A/ja

2014-07-03 Publication of JP2013526560A5 publication Critical patent/JP2013526560A5/ja

Status Pending legal-status Critical Current

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

JP2013510619A 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 Pending JP2013526560A (ja)