JP2015521999A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2015521999A5 JP2015521999A5 JP2015519353A JP2015519353A JP2015521999A5 JP 2015521999 A5 JP2015521999 A5 JP 2015521999A5 JP 2015519353 A JP2015519353 A JP 2015519353A JP 2015519353 A JP2015519353 A JP 2015519353A JP 2015521999 A5 JP2015521999 A5 JP 2015521999A5
- Authority
- JP
- Japan
- Prior art keywords
- dioxide
- benzothiadiazin
- pyrido
- methoxybenzyl
- difluoro
- 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.)
- Granted
Links
- -1 3,5-difluoropyridin-2-yl Chemical group 0.000 claims 24
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- VTGVYRYFFCPVDP-UHFFFAOYSA-N 2-(2,6-dimethoxypyridin-4-yl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound COC1=NC(OC)=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)F)C2=O)(=O)=O)=C1 VTGVYRYFFCPVDP-UHFFFAOYSA-N 0.000 claims 2
- QDQGJOPFXQZYOA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]pyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CN=C2N(CC=2C(=CC(F)=CC=2F)F)C1=O QDQGJOPFXQZYOA-UHFFFAOYSA-N 0.000 claims 2
- BFNAITBFTJKMST-UHFFFAOYSA-N 2-(4,5-dimethoxypyrimidin-2-yl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound N1=C(OC)C(OC)=CN=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(F)=CC=2F)F)C1=O BFNAITBFTJKMST-UHFFFAOYSA-N 0.000 claims 2
- AMOOPKAHWQXYHJ-UHFFFAOYSA-N 2-(4-methoxy-3,5-dimethylphenyl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=C(C)C(OC)=C(C)C=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(F)=CC=2F)F)C1=O AMOOPKAHWQXYHJ-UHFFFAOYSA-N 0.000 claims 2
- SXZSRZJAVCBXPN-UHFFFAOYSA-N 2-(5,6-dimethoxypyridin-3-yl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound N1=C(OC)C(OC)=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)F)C2=O)(=O)=O)=C1 SXZSRZJAVCBXPN-UHFFFAOYSA-N 0.000 claims 2
- SIHACWXKJDLFQA-UHFFFAOYSA-N 2-(5-methoxy-6-methylpyridin-3-yl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]pyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound N1=C(C)C(OC)=CC(N2S(C3=CC=CN=C3N(CC=3C(=CC(F)=CC=3F)F)C2=O)(=O)=O)=C1 SIHACWXKJDLFQA-UHFFFAOYSA-N 0.000 claims 2
- QUHTWFRBBYLQFN-UHFFFAOYSA-N 2-[2-(dimethylamino)pyridin-4-yl]-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=NC(N(C)C)=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)F)C2=O)(=O)=O)=C1 QUHTWFRBBYLQFN-UHFFFAOYSA-N 0.000 claims 2
- QLQCMLQYXKYABM-UHFFFAOYSA-N 2-[6-(dimethylamino)pyridin-2-yl]-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound CN(C)C1=CC=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)F)C2=O)(=O)=O)=N1 QLQCMLQYXKYABM-UHFFFAOYSA-N 0.000 claims 2
- UTZLSYMEXBZFCF-UHFFFAOYSA-N 2-[6-methoxy-5-(methylamino)pyridin-2-yl]-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]pyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound N1=C(OC)C(NC)=CC=C1N1S(=O)(=O)C2=CC=CN=C2N(CC=2C(=CC(F)=CC=2F)F)C1=O UTZLSYMEXBZFCF-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- RMBNGLIVDAWPOZ-UHFFFAOYSA-N 4-[(2,6-difluoro-4-hydroxyphenyl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(O)=CC=2F)F)C1=O RMBNGLIVDAWPOZ-UHFFFAOYSA-N 0.000 claims 2
- CMHMTFXCDBXJMB-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(2,6-dimethoxypyridin-4-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2C=C(OC)N=C(OC)C=2)C1=O CMHMTFXCDBXJMB-UHFFFAOYSA-N 0.000 claims 2
- XYGDSOVVRSIFLQ-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(2,6-dimethoxypyridin-4-yl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=NC=CC=C2S(=O)(=O)N(C=2C=C(OC)N=C(OC)C=2)C1=O XYGDSOVVRSIFLQ-UHFFFAOYSA-N 0.000 claims 2
- OAIUFGDNOLLZRN-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(2-methoxypyridin-4-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2C=C(OC)N=CC=2)C1=O OAIUFGDNOLLZRN-UHFFFAOYSA-N 0.000 claims 2
- AESOLJVLORXMKZ-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2C=C(OC)C(OC)=CC=2)C1=O AESOLJVLORXMKZ-UHFFFAOYSA-N 0.000 claims 2
- KZYDDRNQVBIDMN-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(4,6-dimethoxypyridin-2-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2N=C(OC)C=C(OC)C=2)C1=O KZYDDRNQVBIDMN-UHFFFAOYSA-N 0.000 claims 2
- FWDBCAJERPKMFU-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(4,6-dimethylpyridin-2-yl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=NC=CC=C2S(=O)(=O)N(C=2N=C(C)C=C(C)C=2)C1=O FWDBCAJERPKMFU-UHFFFAOYSA-N 0.000 claims 2
- QOTGHXYPPBLQHV-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(5,6-dimethoxypyridin-2-yl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=NC=CC=C2S(=O)(=O)N(C=2N=C(OC)C(OC)=CC=2)C1=O QOTGHXYPPBLQHV-UHFFFAOYSA-N 0.000 claims 2
- AIZXGTQGJBGNNH-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(5,6-dimethoxypyridin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2C=C(OC)C(OC)=NC=2)C1=O AIZXGTQGJBGNNH-UHFFFAOYSA-N 0.000 claims 2
- UKCZRBZOMBLUFO-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(5,6-dimethoxypyridin-3-yl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=NC=CC=C2S(=O)(=O)N(C=2C=C(OC)C(OC)=NC=2)C1=O UKCZRBZOMBLUFO-UHFFFAOYSA-N 0.000 claims 2
- BDJJTXLVDJSWCD-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(5,6-dimethylpyridin-2-yl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=NC=CC=C2S(=O)(=O)N(C=2N=C(C)C(C)=CC=2)C1=O BDJJTXLVDJSWCD-UHFFFAOYSA-N 0.000 claims 2
- JAYBDSUDRFSLHG-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(5,6-dimethylpyridin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2C=C(C)C(C)=NC=2)C1=O JAYBDSUDRFSLHG-UHFFFAOYSA-N 0.000 claims 2
- HZQQXXNIPZVRPW-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(6-methoxy-5-methylpyridin-2-yl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=NC=CC=C2S(=O)(=O)N(C=2N=C(OC)C(C)=CC=2)C1=O HZQQXXNIPZVRPW-UHFFFAOYSA-N 0.000 claims 2
- NBFUMAFSOCRGBO-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(6-methoxy-5-methylpyridin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2C=C(C)C(OC)=NC=2)C1=O NBFUMAFSOCRGBO-UHFFFAOYSA-N 0.000 claims 2
- YYGUAMUVQOGVEX-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-[5-methyl-6-(methylamino)pyridin-3-yl]-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound C1=C(C)C(NC)=NC=C1N1S(=O)(=O)C2=CC=CN=C2N(CC=2C(=CC(OC)=CC=2F)F)C1=O YYGUAMUVQOGVEX-UHFFFAOYSA-N 0.000 claims 2
- FRTWAZCPGVVGAL-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-[6-methoxy-5-(methylamino)pyridin-3-yl]-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound N1=C(OC)C(NC)=CC(N2S(C3=CC=CN=C3N(CC=3C(=CC(OC)=CC=3F)F)C2=O)(=O)=O)=C1 FRTWAZCPGVVGAL-UHFFFAOYSA-N 0.000 claims 2
- PIZKUXDAZYHUDC-UHFFFAOYSA-N 4-[(2,6-difluorophenyl)methyl]-2-(2,6-dimethoxypyridin-4-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound COC1=NC(OC)=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC=CC=3F)F)C2=O)(=O)=O)=C1 PIZKUXDAZYHUDC-UHFFFAOYSA-N 0.000 claims 2
- AENCEGNWQJYIAV-UHFFFAOYSA-N 4-[(2,6-difluorophenyl)methyl]-2-(5,6-dimethoxypyridin-2-yl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound N1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CN=C2N(CC=2C(=CC=CC=2F)F)C1=O AENCEGNWQJYIAV-UHFFFAOYSA-N 0.000 claims 2
- AZAANRKVBSCLCL-UHFFFAOYSA-N 4-[(2-chloro-4,6-difluorophenyl)methyl]-2-(2,6-dimethoxypyridin-4-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound COC1=NC(OC)=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)Cl)C2=O)(=O)=O)=C1 AZAANRKVBSCLCL-UHFFFAOYSA-N 0.000 claims 2
- WNDPBAFZNGUNGK-UHFFFAOYSA-N 4-[(2-chloro-4,6-difluorophenyl)methyl]-2-(2,6-dimethoxypyridin-4-yl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound COC1=NC(OC)=CC(N2S(C3=CC=CN=C3N(CC=3C(=CC(F)=CC=3F)Cl)C2=O)(=O)=O)=C1 WNDPBAFZNGUNGK-UHFFFAOYSA-N 0.000 claims 2
- ZVQWWVVTWJLQAK-UHFFFAOYSA-N 4-[(2-chloro-4,6-difluorophenyl)methyl]-2-(5,6-dimethoxypyridin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound N1=C(OC)C(OC)=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)Cl)C2=O)(=O)=O)=C1 ZVQWWVVTWJLQAK-UHFFFAOYSA-N 0.000 claims 2
- FWIRKGXMVCCMOY-UHFFFAOYSA-N 4-[(2-chloro-4,6-difluorophenyl)methyl]-2-(5,6-dimethoxypyridin-3-yl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound N1=C(OC)C(OC)=CC(N2S(C3=CC=CN=C3N(CC=3C(=CC(F)=CC=3F)Cl)C2=O)(=O)=O)=C1 FWIRKGXMVCCMOY-UHFFFAOYSA-N 0.000 claims 2
- ARZIDKSCLITHPX-UHFFFAOYSA-N 4-[(2-chloro-6-fluoro-4-methoxyphenyl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound ClC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2C=C(OC)C(OC)=CC=2)C1=O ARZIDKSCLITHPX-UHFFFAOYSA-N 0.000 claims 2
- QZHYUVQJPANIPR-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-(2,6-dimethoxypyridin-4-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound COC1=NC(OC)=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC=CC=3F)Cl)C2=O)(=O)=O)=C1 QZHYUVQJPANIPR-UHFFFAOYSA-N 0.000 claims 2
- DNKOERWWQFHZRF-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-(5,6-dimethoxypyridin-2-yl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound N1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CN=C2N(CC=2C(=CC=CC=2F)Cl)C1=O DNKOERWWQFHZRF-UHFFFAOYSA-N 0.000 claims 2
- JZRNXNOVZOEUII-UHFFFAOYSA-N 4-[(4-chloro-2,6-difluorophenyl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CN=C2N(CC=2C(=CC(Cl)=CC=2F)F)C1=O JZRNXNOVZOEUII-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000006561 Cluster Headache Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 208000019505 Deglutition disease Diseases 0.000 claims 2
- 208000027109 Headache disease Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 2
- 208000018912 cluster headache syndrome Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 206010022437 insomnia Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- GBTROXQFIXAXHR-UHFFFAOYSA-N 1,1-dioxo-2-[(2-oxo-1h-quinolin-4-yl)methyl]-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(F)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(CC=2C3=CC=CC=C3NC(=O)C=2)C1=O GBTROXQFIXAXHR-UHFFFAOYSA-N 0.000 claims 1
- UUJOXQPDKDCXMD-UHFFFAOYSA-N 2-(1,3-benzothiazol-6-yl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1lambda6,2,4-benzothiadiazin-3-one Chemical compound Fc1cc(F)c(CN2C(=O)N(c3ccc4ncsc4c3)S(=O)(=O)c3ccccc23)c(F)c1 UUJOXQPDKDCXMD-UHFFFAOYSA-N 0.000 claims 1
- UADYRZISHAFQDN-UHFFFAOYSA-N 2-(1,3-benzothiazol-6-yl)-4-[(2,6-difluoro-4-methoxyphenyl)methyl]-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=NC=CC=C2S(=O)(=O)N(C=2C=C3SC=NC3=CC=2)C1=O UADYRZISHAFQDN-UHFFFAOYSA-N 0.000 claims 1
- IMYZYCPBPQRRCC-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(F)=CC=2F)F)C1=O IMYZYCPBPQRRCC-UHFFFAOYSA-N 0.000 claims 1
- DUYAPNTXEUGYOZ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-4-[(2,4-dimethylpyridin-3-yl)methyl]-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=NC=CC=2C)C)C1=O DUYAPNTXEUGYOZ-UHFFFAOYSA-N 0.000 claims 1
- ZVAWTSYGPRYQOM-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-4-[(3,5-dimethylpyridin-2-yl)methyl]-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(C)=CN=2)C)C1=O ZVAWTSYGPRYQOM-UHFFFAOYSA-N 0.000 claims 1
- CCXJJZPFZWBSGJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-4-[(3-fluoropyridin-2-yl)methyl]-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC=CN=2)F)C1=O CCXJJZPFZWBSGJ-UHFFFAOYSA-N 0.000 claims 1
- HBIMQHXOIREUGR-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]pyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound C1=C(C)C(C)=CC=C1N1S(=O)(=O)C2=CC=CN=C2N(CC=2C(=CC(F)=CC=2F)F)C1=O HBIMQHXOIREUGR-UHFFFAOYSA-N 0.000 claims 1
- ABLMGALHEKRNBG-UHFFFAOYSA-N 2-(3,5-dimethylphenyl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]pyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound CC1=CC(C)=CC(N2S(C3=CC=CN=C3N(CC=3C(=CC(F)=CC=3F)F)C2=O)(=O)=O)=C1 ABLMGALHEKRNBG-UHFFFAOYSA-N 0.000 claims 1
- BXOCIBRSPQLGLH-UHFFFAOYSA-N 2-(3-methylsulfonylphenyl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1lambda6,2,4-benzothiadiazin-3-one Chemical compound CS(=O)(=O)c1cccc(c1)N1C(=O)N(Cc2c(F)cc(F)cc2F)c2ccccc2S1(=O)=O BXOCIBRSPQLGLH-UHFFFAOYSA-N 0.000 claims 1
- XLGNPBPCOJWPIK-UHFFFAOYSA-N 2-(4-hydroxy-3,5-dimethylphenyl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound CC1=C(O)C(C)=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)F)C2=O)(=O)=O)=C1 XLGNPBPCOJWPIK-UHFFFAOYSA-N 0.000 claims 1
- BZJWRDVQSQEQSK-UHFFFAOYSA-N 2-(5,6-dimethoxypyridin-2-yl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound N1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(F)=CC=2F)F)C1=O BZJWRDVQSQEQSK-UHFFFAOYSA-N 0.000 claims 1
- IRIQVPBCUYSQHO-UHFFFAOYSA-N 2-(5-methylsulfanylpyridin-3-yl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound CSC1=CN=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)F)C2=O)(=O)=O)=C1 IRIQVPBCUYSQHO-UHFFFAOYSA-N 0.000 claims 1
- AGPJDBMVXYQOEJ-UHFFFAOYSA-N 2-(6-methoxypyridin-2-yl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound COC1=CC=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)F)C2=O)(=O)=O)=N1 AGPJDBMVXYQOEJ-UHFFFAOYSA-N 0.000 claims 1
- PVJDBJGTQHGUTI-UHFFFAOYSA-N 2-(6-methylsulfanylpyridin-3-yl)-1,1-dioxo-4-[(2,4,6-trifluorophenyl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=NC(SC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(F)=CC=2F)F)C1=O PVJDBJGTQHGUTI-UHFFFAOYSA-N 0.000 claims 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
- LPPIIVYMLMVMQT-UHFFFAOYSA-N 4-[(2,4-difluoro-6-methoxyphenyl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(F)=CC=2F)OC)C1=O LPPIIVYMLMVMQT-UHFFFAOYSA-N 0.000 claims 1
- JMQSGKGGUHFJPB-UHFFFAOYSA-N 4-[(2,5-dimethylpyrazol-3-yl)methyl]-2-(3-methylsulfanylphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound CSC1=CC=CC(N2S(C3=CC=CC=C3N(CC=3N(N=C(C)C=3)C)C2=O)(=O)=O)=C1 JMQSGKGGUHFJPB-UHFFFAOYSA-N 0.000 claims 1
- VEMPRPJLBGNBKN-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=NC=CC=C2S(=O)(=O)N(C=2C=C(OC)C(OC)=CC=2)C1=O VEMPRPJLBGNBKN-UHFFFAOYSA-N 0.000 claims 1
- ZGICPKBLTQJTAX-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(3,4-dimethylphenyl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=NC=CC=C2S(=O)(=O)N(C=2C=C(C)C(C)=CC=2)C1=O ZGICPKBLTQJTAX-UHFFFAOYSA-N 0.000 claims 1
- KUPWMKUIBYLMCT-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(3-methylsulfanylphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2C=C(SC)C=CC=2)C1=O KUPWMKUIBYLMCT-UHFFFAOYSA-N 0.000 claims 1
- FCFAOSSZIVPZRA-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(3-methylsulfonylphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2C=C(C=CC=2)S(C)(=O)=O)C1=O FCFAOSSZIVPZRA-UHFFFAOYSA-N 0.000 claims 1
- RMCOEZZSFFSADO-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(5,6-dimethoxypyridin-2-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2N=C(OC)C(OC)=CC=2)C1=O RMCOEZZSFFSADO-UHFFFAOYSA-N 0.000 claims 1
- MGWGPFFHHLSKHF-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(6-methoxypyridin-2-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2N=C(OC)C=CC=2)C1=O MGWGPFFHHLSKHF-UHFFFAOYSA-N 0.000 claims 1
- GNZNXJPENLZMPC-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-(6-methoxypyridin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2C=NC(OC)=CC=2)C1=O GNZNXJPENLZMPC-UHFFFAOYSA-N 0.000 claims 1
- GNHHCOGBCPQIDC-UHFFFAOYSA-N 4-[(2,6-difluoro-4-methoxyphenyl)methyl]-2-[5-methoxy-6-(methylamino)pyridin-3-yl]-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound C1=C(OC)C(NC)=NC=C1N1S(=O)(=O)C2=CC=CN=C2N(CC=2C(=CC(OC)=CC=2F)F)C1=O GNHHCOGBCPQIDC-UHFFFAOYSA-N 0.000 claims 1
- MUMIGVNNLOFKPQ-UHFFFAOYSA-N 4-[(2,6-difluorophenyl)methyl]-1,1-dioxo-2-[(2-oxo-1h-quinolin-4-yl)methyl]-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(CC=2C3=CC=CC=C3NC(=O)C=2)C1=O MUMIGVNNLOFKPQ-UHFFFAOYSA-N 0.000 claims 1
- YDNAVCHJMIUOMH-UHFFFAOYSA-N 4-[(2,6-difluorophenyl)methyl]-2-(1-ethylpiperidin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1N(CC)CCCC1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC=CC=2F)F)C1=O YDNAVCHJMIUOMH-UHFFFAOYSA-N 0.000 claims 1
- QQLXWOIQZKSBRW-UHFFFAOYSA-N 4-[(2,6-difluorophenyl)methyl]-2-[(1-methylimidazol-2-yl)methyl]-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound CN1C=CN=C1CN1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC=CC=2F)F)C1=O QQLXWOIQZKSBRW-UHFFFAOYSA-N 0.000 claims 1
- INSMCISRZKKASA-UHFFFAOYSA-N 4-[(2,6-difluorophenyl)methyl]-2-[(1-methylindazol-3-yl)methyl]-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C12=CC=CC=C2N(C)N=C1CN(S(C1=CC=CC=C11)(=O)=O)C(=O)N1CC1=C(F)C=CC=C1F INSMCISRZKKASA-UHFFFAOYSA-N 0.000 claims 1
- RFRFIIVJPKJXAZ-UHFFFAOYSA-N 4-[(2,6-difluorophenyl)methyl]-2-[(2-methyl-1,3-thiazol-4-yl)methyl]-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound S1C(C)=NC(CN2S(C3=CC=CC=C3N(CC=3C(=CC=CC=3F)F)C2=O)(=O)=O)=C1 RFRFIIVJPKJXAZ-UHFFFAOYSA-N 0.000 claims 1
- MCUARPBOYFTGBE-UHFFFAOYSA-N 4-[(2,6-difluorophenyl)methyl]-2-[(3,4-dimethoxypyridin-2-yl)methyl]-1,1-dioxo-1lambda6,2,4-benzothiadiazin-3-one Chemical compound COc1ccnc(CN2C(=O)N(Cc3c(F)cccc3F)c3ccccc3S2(=O)=O)c1OC MCUARPBOYFTGBE-UHFFFAOYSA-N 0.000 claims 1
- SLVXFAHQHVKXOO-UHFFFAOYSA-N 4-[(2,6-difluorophenyl)methyl]-2-[2-(3,5-dimethyl-1,2-oxazol-4-yl)ethyl]-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound CC1=NOC(C)=C1CCN1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC=CC=2F)F)C1=O SLVXFAHQHVKXOO-UHFFFAOYSA-N 0.000 claims 1
- MEJPCZPAVFCDKK-UHFFFAOYSA-N 4-[(2-chloro-4,6-difluorophenyl)methyl]-2-(2-methoxypyridin-4-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=NC(OC)=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)Cl)C2=O)(=O)=O)=C1 MEJPCZPAVFCDKK-UHFFFAOYSA-N 0.000 claims 1
- QGLYNZFFEWJHNU-UHFFFAOYSA-N 4-[(2-chloro-4,6-difluorophenyl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(F)=CC=2F)Cl)C1=O QGLYNZFFEWJHNU-UHFFFAOYSA-N 0.000 claims 1
- ZNKFURURHVQZFU-UHFFFAOYSA-N 4-[(2-chloro-4,6-difluorophenyl)methyl]-2-(3-methylsulfanylphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound CSC1=CC=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)Cl)C2=O)(=O)=O)=C1 ZNKFURURHVQZFU-UHFFFAOYSA-N 0.000 claims 1
- IGAOPYZSBQCAIV-UHFFFAOYSA-N 4-[(2-chloro-4,6-difluorophenyl)methyl]-2-(5,6-dimethoxypyridin-2-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound N1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(F)=CC=2F)Cl)C1=O IGAOPYZSBQCAIV-UHFFFAOYSA-N 0.000 claims 1
- QGIUCOOZFZZBBD-UHFFFAOYSA-N 4-[(2-chloro-4,6-difluorophenyl)methyl]-2-(6-methoxypyridin-2-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound COC1=CC=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC(F)=CC=3F)Cl)C2=O)(=O)=O)=N1 QGIUCOOZFZZBBD-UHFFFAOYSA-N 0.000 claims 1
- LBLLYXVBNXRFAH-UHFFFAOYSA-N 4-[(2-chloro-6-fluoro-4-methoxyphenyl)methyl]-2-(6-methoxypyridin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound ClC1=CC(OC)=CC(F)=C1CN1C2=CC=CC=C2S(=O)(=O)N(C=2C=NC(OC)=CC=2)C1=O LBLLYXVBNXRFAH-UHFFFAOYSA-N 0.000 claims 1
- QGFAKWRJFLFBNG-UHFFFAOYSA-N 4-[(2-chloro-6-fluoro-4-methylphenyl)methyl]-2-(6-methoxypyridin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=NC(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(C)=CC=2F)Cl)C1=O QGFAKWRJFLFBNG-UHFFFAOYSA-N 0.000 claims 1
- ZATHTCWOOIKFPO-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-1,1-dioxo-2-(pyridin-2-ylmethyl)-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC=CC(Cl)=C1CN1C2=CC=CC=C2S(=O)(=O)N(CC=2N=CC=CC=2)C1=O ZATHTCWOOIKFPO-UHFFFAOYSA-N 0.000 claims 1
- QTVGNYBODUFRLN-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-(1-ethylpyrazol-4-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=NN(CC)C=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC=CC=2F)Cl)C1=O QTVGNYBODUFRLN-UHFFFAOYSA-N 0.000 claims 1
- LYWVDNWUWYNJDY-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-(2-methoxypyridin-4-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=NC(OC)=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC=CC=3F)Cl)C2=O)(=O)=O)=C1 LYWVDNWUWYNJDY-UHFFFAOYSA-N 0.000 claims 1
- FTIAKLCUESOASV-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-(2-methoxypyrimidin-5-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=NC(OC)=NC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC=CC=2F)Cl)C1=O FTIAKLCUESOASV-UHFFFAOYSA-N 0.000 claims 1
- RQHRQPXBIZVWHA-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxopyrido[2,3-e][1,2,4]thiadiazin-3-one Chemical compound COc1ccc(cc1OC)N1C(=O)N(Cc2c(F)cccc2Cl)c2ncccc2S1(=O)=O RQHRQPXBIZVWHA-UHFFFAOYSA-N 0.000 claims 1
- LIQOXHSGVADLHH-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxopyrido[4,3-e][1,2,4]thiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CN=CC=C2N(CC=2C(=CC=CC=2F)Cl)C1=O LIQOXHSGVADLHH-UHFFFAOYSA-N 0.000 claims 1
- VPXGBSDNICONID-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-(5-methylsulfanylpyridin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound CSC1=CN=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC=CC=3F)Cl)C2=O)(=O)=O)=C1 VPXGBSDNICONID-UHFFFAOYSA-N 0.000 claims 1
- ALIUNUOUZSRWBI-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-(6-methoxypyridin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=NC(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC=CC=2F)Cl)C1=O ALIUNUOUZSRWBI-UHFFFAOYSA-N 0.000 claims 1
- CLNKXYJLIJBTJG-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-(6-methylpyridin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=NC(C)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC=CC=2F)Cl)C1=O CLNKXYJLIJBTJG-UHFFFAOYSA-N 0.000 claims 1
- LJTTVBKRMFLGFV-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-(oxan-4-ylmethyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound FC1=CC=CC(Cl)=C1CN1C2=CC=CC=C2S(=O)(=O)N(CC2CCOCC2)C1=O LJTTVBKRMFLGFV-UHFFFAOYSA-N 0.000 claims 1
- LIWNNZBTALMNIP-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-[(2,5-dimethylpyrazol-3-yl)methyl]-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound CN1N=C(C)C=C1CN1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC=CC=2F)Cl)C1=O LIWNNZBTALMNIP-UHFFFAOYSA-N 0.000 claims 1
- SCLQIPLAIONUMO-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-[(3-methyloxetan-3-yl)methyl]-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound O=C1N(CC=2C(=CC=CC=2F)Cl)C2=CC=CC=C2S(=O)(=O)N1CC1(C)COC1 SCLQIPLAIONUMO-UHFFFAOYSA-N 0.000 claims 1
- OPICLJFAIOKPJI-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-2-[(5-methyl-1,2-oxazol-3-yl)methyl]-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound O1C(C)=CC(CN2S(C3=CC=CC=C3N(CC=3C(=CC=CC=3F)Cl)C2=O)(=O)=O)=N1 OPICLJFAIOKPJI-UHFFFAOYSA-N 0.000 claims 1
- ICXWZQMSBWEYAB-UHFFFAOYSA-N 4-[(2-chloro-6-fluorophenyl)methyl]-5-fluoro-2-(6-methoxypyridin-3-yl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=NC(OC)=CC=C1N1S(=O)(=O)C2=CC=CC(F)=C2N(CC=2C(=CC=CC=2F)Cl)C1=O ICXWZQMSBWEYAB-UHFFFAOYSA-N 0.000 claims 1
- WEOFTYZTFCZLDE-UHFFFAOYSA-N 4-[(3,5-dichloropyridin-4-yl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CN=CC=2Cl)Cl)C1=O WEOFTYZTFCZLDE-UHFFFAOYSA-N 0.000 claims 1
- OECPLGPCIVCADN-UHFFFAOYSA-N 4-[(3,5-difluoropyridin-4-yl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CN=CC=2F)F)C1=O OECPLGPCIVCADN-UHFFFAOYSA-N 0.000 claims 1
- UGBRNOSOHAXEEC-UHFFFAOYSA-N 4-[(3-methylpyridin-2-yl)methyl]-2-(3-methylsulfanylphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound CSC1=CC=CC(N2S(C3=CC=CC=C3N(CC=3C(=CC=CN=3)C)C2=O)(=O)=O)=C1 UGBRNOSOHAXEEC-UHFFFAOYSA-N 0.000 claims 1
- HECLWHLEJILNDZ-UHFFFAOYSA-N 4-[(4-chloro-2-fluorophenyl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxopyrido[4,3-e][1,2,4]thiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CN=CC=C2N(CC=2C(=CC(Cl)=CC=2)F)C1=O HECLWHLEJILNDZ-UHFFFAOYSA-N 0.000 claims 1
- XQUIZWVARDQJLF-UHFFFAOYSA-N 4-[(4-chloro-2-fluorophenyl)methyl]-2-[(2,5-dimethylpyrazol-3-yl)methyl]-1,1-dioxo-1lambda6,2,4-benzothiadiazin-3-one Chemical compound Cc1cc(CN2C(=O)N(Cc3ccc(Cl)cc3F)c3ccccc3S2(=O)=O)n(C)n1 XQUIZWVARDQJLF-UHFFFAOYSA-N 0.000 claims 1
- AMGYOOJFCQIPLQ-UHFFFAOYSA-N 4-[(5-bromo-3-fluoropyridin-2-yl)methyl]-2-(3,4-dimethoxyphenyl)-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2N(CC=2C(=CC(Br)=CN=2)F)C1=O AMGYOOJFCQIPLQ-UHFFFAOYSA-N 0.000 claims 1
- 208000030990 Impulse-control disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 108050000742 Orexin Receptor Proteins 0.000 claims 1
- 102000008834 Orexin receptor Human genes 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 0 CN(C(C(S(N1*)(=O)=O)=**=**)=I)C1=O Chemical compound CN(C(C(S(N1*)(=O)=O)=**=**)=I)C1=O 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261667540P | 2012-07-03 | 2012-07-03 | |
| US61/667,540 | 2012-07-03 | ||
| PCT/GB2013/051761 WO2014006402A1 (en) | 2012-07-03 | 2013-07-03 | Orexin receptor antagonists |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018072560A Division JP6424285B2 (ja) | 2012-07-03 | 2018-04-04 | オレキシン受容体アンタゴニスト |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015521999A JP2015521999A (ja) | 2015-08-03 |
| JP2015521999A5 true JP2015521999A5 (enExample) | 2016-08-18 |
| JP6484553B2 JP6484553B2 (ja) | 2019-03-13 |
Family
ID=48746574
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015519353A Expired - Fee Related JP6484553B2 (ja) | 2012-07-03 | 2013-07-03 | オレキシン受容体アンタゴニスト |
| JP2018072560A Active JP6424285B2 (ja) | 2012-07-03 | 2018-04-04 | オレキシン受容体アンタゴニスト |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018072560A Active JP6424285B2 (ja) | 2012-07-03 | 2018-04-04 | オレキシン受容体アンタゴニスト |
Country Status (5)
| Country | Link |
|---|---|
| US (4) | US9249160B2 (enExample) |
| EP (1) | EP2870144B1 (enExample) |
| JP (2) | JP6484553B2 (enExample) |
| BR (1) | BR112015000176A2 (enExample) |
| WO (1) | WO2014006402A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2870144B1 (en) | 2012-07-03 | 2017-04-19 | Heptares Therapeutics Limited | Orexin receptor antagonists |
| WO2016130043A1 (ru) * | 2015-02-13 | 2016-08-18 | Александ Васильевич ИВАЩЕНКО | Бензо[1,2,4]тиадиазиновые ингибиторы репликации вируса гепатита в и фармацевтическая композиция для лечения гепатита в |
| CA2989146A1 (en) | 2015-06-12 | 2016-12-15 | Board Of Regents, The University Of Texas System | Sulfonamide derivative and pharmaceutically acceptable acid addition salt thereof |
| SG11201806429PA (en) * | 2016-02-04 | 2018-08-30 | Takeda Pharmaceuticals Co | Substituted piperidine compound and use thereof |
| CN107179356B (zh) * | 2016-03-11 | 2021-07-16 | 广东东阳光药业有限公司 | 一种用hplc法测定苏沃雷生有关物质的方法 |
| RU2662161C1 (ru) * | 2017-08-11 | 2018-07-24 | Васильевич Иващенко Александр | Ингибитор входа вируса гепатита и фармацевтическая композиция для лечения гепатита |
| GB201718256D0 (en) * | 2017-11-03 | 2017-12-20 | Heptares Therapeutics Ltd | Ox1 antagonists |
| JP7170996B2 (ja) * | 2017-12-12 | 2022-11-15 | 国立大学法人 筑波大学 | スルホンアミド誘導体またはその薬学的に許容される酸付加塩 |
| SG11202106108WA (en) | 2019-01-28 | 2021-08-30 | Suntory Holdings Ltd | Composition for competitive inhibition of orexin receptors |
| US11098029B2 (en) | 2019-02-13 | 2021-08-24 | Merck Sharp & Dohme Corp. | 5-alkyl pyrrolidine orexin receptor agonists |
| JP7833486B2 (ja) | 2021-05-26 | 2026-03-19 | アルカーメス，インコーポレイテッド | 置換されるカルバメート大環状化合物および関連のある治療方法 |
| AU2024275892A1 (en) * | 2023-05-23 | 2026-01-22 | Institute For Cancer Research D/B/A The Research Institute Of Fox Chase Cancer Center | Compounds that re-activate mutant p53 |
| CN122374291A (zh) | 2023-12-12 | 2026-07-10 | 爱杜西亚药品有限公司 | 作为食欲素受体调节剂的芳基砜及砜酮衍生物 |
| WO2025132542A1 (en) | 2023-12-19 | 2025-06-26 | Idorsia Pharmaceuticals Ltd | Macrocyclic orexin agonists |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5642897A (en) * | 1979-09-17 | 1981-04-21 | Tokyo Shibaura Electric Co | Display unit |
| DE3835291A1 (de) | 1988-04-19 | 1989-11-02 | Bayer Ag | 1,3-disubstituierte pyrrolidine |
| JP3000943B2 (ja) | 1996-07-02 | 2000-01-17 | トヨタ自動車株式会社 | 動力出力装置およびその制御方法 |
| DE19952146A1 (de) | 1999-10-29 | 2001-06-07 | Boehringer Ingelheim Pharma | Arylalkane, Arylalkene und Aryl-azaalkane, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US6774134B2 (en) | 2000-12-20 | 2004-08-10 | Bristol-Myers Squibb Company | Heterocyclic substituted 2-methyl-benzimidazole antiviral agents |
| WO2002051232A2 (en) * | 2000-12-27 | 2002-07-04 | Actelion Pharmaceuticals Ltd. | Novel benzazepines and related heterocyclic derivatives |
| US6919331B2 (en) | 2001-12-10 | 2005-07-19 | Bristol-Myers Squibb Company | Substituted 2-methyl-benzimidazole respiratory syncytial virus antiviral agents |
| JP2008540574A (ja) * | 2005-05-11 | 2008-11-20 | タケダ サン ディエゴ インコーポレイテッド | ヒストンデアセチラーゼ阻害剤 |
| KR100787130B1 (ko) * | 2006-03-23 | 2007-12-21 | 한국화학연구원 | 신규의 치환된 1,1-다이옥소-벤조[1,2,4]티아디아진-3-온, 이의 제조방법 및 이를 포함하는 약학적 조성물 |
| EP2049110B1 (en) * | 2006-07-14 | 2014-08-20 | Merck Sharp & Dohme Corp. | Bridged diazepan orexin receptor antagonists |
| EP2870144B1 (en) * | 2012-07-03 | 2017-04-19 | Heptares Therapeutics Limited | Orexin receptor antagonists |
| JP2018072560A (ja) * | 2016-10-28 | 2018-05-10 | 富士通株式会社 | 情報処理システム、情報処理装置及び情報処理方法 |
-
2013
- 2013-07-03 EP EP13734146.7A patent/EP2870144B1/en active Active
- 2013-07-03 JP JP2015519353A patent/JP6484553B2/ja not_active Expired - Fee Related
- 2013-07-03 WO PCT/GB2013/051761 patent/WO2014006402A1/en not_active Ceased
- 2013-07-03 BR BR112015000176A patent/BR112015000176A2/pt not_active Application Discontinuation
- 2013-07-03 US US14/411,269 patent/US9249160B2/en active Active
-
2016
- 2016-01-13 US US14/994,607 patent/US9555044B2/en active Active
-
2017
- 2017-01-18 US US15/409,246 patent/US9850237B2/en active Active
- 2017-12-20 US US15/848,771 patent/US10316028B2/en active Active
-
2018
- 2018-04-04 JP JP2018072560A patent/JP6424285B2/ja active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2012102908A (ru) | Азаадамантановые производные и способы применения | |
| JP2013545744A5 (enExample) | ||
| RU2015100942A (ru) | Производное пиперидинилпиразолпиридина | |
| JP2004536814A5 (enExample) | ||
| RU2015107979A (ru) | Новые бициклические производные пиридина | |
| ME01308B (me) | Jedinjenja biaril etra uree | |
| RU2015132181A (ru) | Фтор-[1,3]-оксазины в качестве ингибиторов васе1 | |
| RU2012105284A (ru) | Спиро-аминосоединения, пригодные для лечения нарушений сна и лекарственного привыкания | |
| RU2018138047A (ru) | Гетероциклические вещества - агонисты gpr119 | |
| IL258577A (en) | 2,4-dihydroxy-nicotinamides as apj agonists | |
| RU2010137300A (ru) | Модуляторы бета-амилоида | |
| JP2015526452A5 (enExample) | ||
| JP2016500073A5 (enExample) | ||
| JP2012508776A5 (enExample) | ||
| HRP20120240T1 (hr) | Piridil piperidin antagonisti receptora za oreksin | |
| JP2018534326A5 (enExample) | ||
| JP2018530591A5 (enExample) | ||
| JP2007523181A5 (enExample) | ||
| JP2016523977A5 (enExample) | ||
| JP2014501269A5 (enExample) | ||
| JP2013544256A5 (enExample) | ||
| RU2007124935A (ru) | АМИНОПИРИДИНЫ В КАЧЕСТВЕ ИНГИБИТОРОВ β-СЕКТРЕТАЗЫ | |
| IL263511A (en) | 1h-pyrazolo[4,3-b]pyridines as pde1 inhibitors | |
| JP2014516989A5 (enExample) | ||
| JP2018520201A5 (enExample) |