JP2015517981A5 - - Google Patents
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- Publication number
- JP2015517981A5 JP2015517981A5 JP2014560012A JP2014560012A JP2015517981A5 JP 2015517981 A5 JP2015517981 A5 JP 2015517981A5 JP 2014560012 A JP2014560012 A JP 2014560012A JP 2014560012 A JP2014560012 A JP 2014560012A JP 2015517981 A5 JP2015517981 A5 JP 2015517981A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- trifluoromethyl
- chloro
- optionally substituted
- methyl
- 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
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- -1 N- (2-chloro-5- (trifluoromethyl) phenyl) phenylsulfonamido Chemical group 0.000 claims 42
- 125000000217 alkyl group Chemical group 0.000 claims 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 239000000203 mixture Substances 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229940002612 prodrugs Drugs 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000011780 sodium chloride Substances 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000004432 carbon atoms Chemical group C* 0.000 claims 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- WXJVIWDGVJRAMG-UHFFFAOYSA-N 4-[benzyl(methyl)sulfamoyl]-N-(2-methyl-1,3-benzothiazol-6-yl)benzamide Chemical compound C=1C=C(C(=O)NC=2C=C3SC(C)=NC3=CC=2)C=CC=1S(=O)(=O)N(C)CC1=CC=CC=C1 WXJVIWDGVJRAMG-UHFFFAOYSA-N 0.000 claims 6
- ZYSVTDOKHHYVMY-UHFFFAOYSA-N 4-[benzyl(methyl)sulfamoyl]-N-(2-methyl-1H-indol-5-yl)benzamide Chemical compound C=1C=C(C(=O)NC=2C=C3C=C(C)NC3=CC=2)C=CC=1S(=O)(=O)N(C)CC1=CC=CC=C1 ZYSVTDOKHHYVMY-UHFFFAOYSA-N 0.000 claims 6
- YCBLVAVPKHSKNW-UHFFFAOYSA-N N-(1,3-benzothiazol-6-yl)-4-[benzyl(methyl)sulfamoyl]benzamide Chemical compound C=1C=C(C(=O)NC=2C=C3SC=NC3=CC=2)C=CC=1S(=O)(=O)N(C)CC1=CC=CC=C1 YCBLVAVPKHSKNW-UHFFFAOYSA-N 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 239000000546 pharmaceutic aid Substances 0.000 claims 4
- FNYVRYJSDITDHH-UHFFFAOYSA-N 1-(benzenesulfonyl)-N-(pyridin-4-ylmethyl)indole-2-carboxamide Chemical compound C=1C2=CC=CC=C2N(S(=O)(=O)C=2C=CC=CC=2)C=1C(=O)NCC1=CC=NC=C1 FNYVRYJSDITDHH-UHFFFAOYSA-N 0.000 claims 3
- DNMMXPBILQAOSG-UHFFFAOYSA-N 1-(benzenesulfonyl)-N-(pyridin-4-ylmethyl)pyrrolidine-2-carboxamide Chemical compound C1CCN(S(=O)(=O)C=2C=CC=CC=2)C1C(=O)NCC1=CC=NC=C1 DNMMXPBILQAOSG-UHFFFAOYSA-N 0.000 claims 3
- LJLZTFHJAZWNGM-UHFFFAOYSA-N 2-[2-chloro-N-(4-fluorophenyl)sulfonyl-5-(trifluoromethyl)anilino]-N-(pyridin-4-ylmethyl)acetamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N(C=1C(=CC=C(C=1)C(F)(F)F)Cl)CC(=O)NCC1=CC=NC=C1 LJLZTFHJAZWNGM-UHFFFAOYSA-N 0.000 claims 3
- HHUMJPUHFJHWDR-UHFFFAOYSA-N 2-[2-chloro-N-(4-methylphenyl)sulfonyl-5-(trifluoromethyl)anilino]-N-(pyridin-4-ylmethyl)acetamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(C=1C(=CC=C(C=1)C(F)(F)F)Cl)CC(=O)NCC1=CC=NC=C1 HHUMJPUHFJHWDR-UHFFFAOYSA-N 0.000 claims 3
- MPUOPJLIYOHBKO-UHFFFAOYSA-N 2-[N-(benzenesulfonyl)-2-bromo-5-(trifluoromethyl)anilino]-N-(pyridin-4-ylmethyl)acetamide Chemical compound FC(F)(F)C1=CC=C(Br)C(N(CC(=O)NCC=2C=CN=CC=2)S(=O)(=O)C=2C=CC=CC=2)=C1 MPUOPJLIYOHBKO-UHFFFAOYSA-N 0.000 claims 3
- YYUQNEGQLXBAAB-UHFFFAOYSA-N 2-[N-(benzenesulfonyl)-2-chloro-5-(trifluoromethyl)anilino]-N-(2-methyl-1,3-benzothiazol-5-yl)acetamide Chemical compound C=1C=C2SC(C)=NC2=CC=1NC(=O)CN(S(=O)(=O)C=1C=CC=CC=1)C1=CC(C(F)(F)F)=CC=C1Cl YYUQNEGQLXBAAB-UHFFFAOYSA-N 0.000 claims 3
- JKZSHWDPOQYSJW-UHFFFAOYSA-N 2-[N-(benzenesulfonyl)-2-chloro-5-(trifluoromethyl)anilino]-N-(pyridin-4-ylmethyl)acetamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(N(CC(=O)NCC=2C=CN=CC=2)S(=O)(=O)C=2C=CC=CC=2)=C1 JKZSHWDPOQYSJW-UHFFFAOYSA-N 0.000 claims 3
- NZOQAZDUNOKANC-UHFFFAOYSA-N 2-[N-(benzenesulfonyl)-2-chloro-5-(trifluoromethyl)anilino]-N-(pyridin-4-ylmethyl)propanamide Chemical compound C=1C=NC=CC=1CNC(=O)C(C)N(S(=O)(=O)C=1C=CC=CC=1)C1=CC(C(F)(F)F)=CC=C1Cl NZOQAZDUNOKANC-UHFFFAOYSA-N 0.000 claims 3
- FLLOQNNOISPJJY-UHFFFAOYSA-N 2-[N-(benzenesulfonyl)-2-chloro-5-(trifluoromethyl)anilino]-N-[(1,1-dimethylpiperidin-1-ium-4-yl)methyl]acetamide;chloride Chemical compound [Cl-].C1C[N+](C)(C)CCC1CNC(=O)CN(S(=O)(=O)C=1C=CC=CC=1)C1=CC(C(F)(F)F)=CC=C1Cl FLLOQNNOISPJJY-UHFFFAOYSA-N 0.000 claims 3
- VIRKBRHDLQVURO-UHFFFAOYSA-N 2-[N-(benzenesulfonyl)-2-chloro-5-(trifluoromethyl)anilino]-N-[[3-(4-methylpiperazin-1-yl)phenyl]methyl]acetamide Chemical compound C1CN(C)CCN1C1=CC=CC(CNC(=O)CN(C=2C(=CC=C(C=2)C(F)(F)F)Cl)S(=O)(=O)C=2C=CC=CC=2)=C1 VIRKBRHDLQVURO-UHFFFAOYSA-N 0.000 claims 3
- CQIQZFVEASLEBW-UHFFFAOYSA-N 2-[N-(benzenesulfonyl)-2-chloro-5-(trifluoromethyl)anilino]-N-[[4-(4-methylpiperazin-1-yl)phenyl]methyl]acetamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1CNC(=O)CN(S(=O)(=O)C=1C=CC=CC=1)C1=CC(C(F)(F)F)=CC=C1Cl CQIQZFVEASLEBW-UHFFFAOYSA-N 0.000 claims 3
- GVZSEENGSUJYNL-UHFFFAOYSA-N 2-[N-(benzenesulfonyl)-2-chloro-5-(trifluoromethyl)anilino]-N-benzylacetamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(N(CC(=O)NCC=2C=CC=CC=2)S(=O)(=O)C=2C=CC=CC=2)=C1 GVZSEENGSUJYNL-UHFFFAOYSA-N 0.000 claims 3
- OSABULQOUJSUJV-UHFFFAOYSA-N 2-[N-(benzenesulfonyl)-2-fluoro-5-(trifluoromethyl)anilino]-N-(pyridin-4-ylmethyl)acetamide Chemical compound FC1=CC=C(C(F)(F)F)C=C1N(S(=O)(=O)C=1C=CC=CC=1)CC(=O)NCC1=CC=NC=C1 OSABULQOUJSUJV-UHFFFAOYSA-N 0.000 claims 3
- IMCULDWFDHJIPO-UHFFFAOYSA-N 4-[benzyl(methyl)sulfamoyl]-N-(2-methyl-1,3-benzothiazol-5-yl)benzamide Chemical compound C=1C=C(C(=O)NC=2C=C3N=C(C)SC3=CC=2)C=CC=1S(=O)(=O)N(C)CC1=CC=CC=C1 IMCULDWFDHJIPO-UHFFFAOYSA-N 0.000 claims 3
- WSQASFGXLBQZIR-UHFFFAOYSA-N 4-[benzyl(methyl)sulfamoyl]-N-(pyridin-4-ylmethyl)benzamide Chemical compound C=1C=C(C(=O)NCC=2C=CN=CC=2)C=CC=1S(=O)(=O)N(C)CC1=CC=CC=C1 WSQASFGXLBQZIR-UHFFFAOYSA-N 0.000 claims 3
- QMYKPBMKPPHOOS-UHFFFAOYSA-N 4-[benzyl(methyl)sulfamoyl]-N-[2-chloro-5-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C(C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)Cl)C=CC=1S(=O)(=O)N(C)CC1=CC=CC=C1 QMYKPBMKPPHOOS-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 3
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 229920002759 Circular DNA Polymers 0.000 claims 2
- 108020004638 Circular DNA Proteins 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 238000005755 formation reaction Methods 0.000 claims 2
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261605071P | 2012-02-29 | 2012-02-29 | |
| US201261605059P | 2012-02-29 | 2012-02-29 | |
| US61/605,071 | 2012-02-29 | ||
| US61/605,059 | 2012-02-29 | ||
| PCT/US2013/028150 WO2013130703A2 (en) | 2012-02-29 | 2013-02-28 | Binhibitors of hepatitis b virus convalently closed circular dna formation and their method of use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017083672A Division JP2017165751A (ja) | 2012-02-29 | 2017-04-20 | Ｂ型肝炎ウイルス共有結合閉環状ｄｎａ形成の阻害剤およびそれらの使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015517981A JP2015517981A (ja) | 2015-06-25 |
| JP2015517981A5 true JP2015517981A5 (US07132539-20061107-C00040.png) | 2016-06-16 |
| JP6134338B2 JP6134338B2 (ja) | 2017-05-24 |
Family
ID=49083449
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014560012A Expired - Fee Related JP6134338B2 (ja) | 2012-02-29 | 2013-02-28 | Ｂ型肝炎ウイルス共有結合閉環状ｄｎａ形成の阻害剤およびそれらの使用方法 |
| JP2017083672A Pending JP2017165751A (ja) | 2012-02-29 | 2017-04-20 | Ｂ型肝炎ウイルス共有結合閉環状ｄｎａ形成の阻害剤およびそれらの使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017083672A Pending JP2017165751A (ja) | 2012-02-29 | 2017-04-20 | Ｂ型肝炎ウイルス共有結合閉環状ｄｎａ形成の阻害剤およびそれらの使用方法 |
Country Status (10)
Families Citing this family (51)
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2013
- 2013-02-28 NZ NZ631419A patent/NZ631419A/en not_active IP Right Cessation
- 2013-02-28 EP EP13755289.9A patent/EP2819671A4/en not_active Withdrawn
- 2013-02-28 WO PCT/US2013/028150 patent/WO2013130703A2/en active Application Filing
- 2013-02-28 AU AU2013226013A patent/AU2013226013B2/en not_active Ceased
- 2013-02-28 CN CN201380011882.5A patent/CN104822267B/zh not_active Expired - Fee Related
- 2013-02-28 US US14/382,074 patent/US9657013B2/en not_active Expired - Fee Related
- 2013-02-28 BR BR112014021498A patent/BR112014021498A2/pt not_active IP Right Cessation
- 2013-02-28 JP JP2014560012A patent/JP6134338B2/ja not_active Expired - Fee Related
- 2013-02-28 CA CA2865962A patent/CA2865962A1/en not_active Abandoned
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2014
- 2014-10-24 ZA ZA2014/07798A patent/ZA201407798B/en unknown
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2016
- 2016-11-02 AU AU2016253583A patent/AU2016253583A1/en not_active Abandoned
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2017
- 2017-04-20 JP JP2017083672A patent/JP2017165751A/ja active Pending
