JP2018515509A5 - - Google Patents
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- Publication number
- JP2018515509A5 JP2018515509A5 JP2017558397A JP2017558397A JP2018515509A5 JP 2018515509 A5 JP2018515509 A5 JP 2018515509A5 JP 2017558397 A JP2017558397 A JP 2017558397A JP 2017558397 A JP2017558397 A JP 2017558397A JP 2018515509 A5 JP2018515509 A5 JP 2018515509A5
- Authority
- JP
- Japan
- Prior art keywords
- purin
- amino
- methyl
- alkyl
- propylsulfonimidoyl
- 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 cyano, carboxy, carbamoyl Chemical group 0.000 claims description 94
- 150000001875 compounds Chemical class 0.000 claims description 47
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- CCVSDUKQNMVXAV-UHFFFAOYSA-N 6-(ethylamino)-9-[(6-methylpyridin-3-yl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound C(C)NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC=1C=NC(=CC=1)C)=O CCVSDUKQNMVXAV-UHFFFAOYSA-N 0.000 claims description 2
- AWEYWRZATBLERV-UHFFFAOYSA-N 9-[(4-chlorophenyl)methyl]-6-(ethylamino)-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NCC)S(=O)(=N)CCC AWEYWRZATBLERV-UHFFFAOYSA-N 0.000 claims description 2
- XYCHAVDXFFLWQJ-UHFFFAOYSA-N 9-benzyl-6-(cyclopropylamino)-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NC1CC1)S(=O)(=N)CCC XYCHAVDXFFLWQJ-UHFFFAOYSA-N 0.000 claims description 2
- QNJDNDBLKCNKGH-UHFFFAOYSA-N 9-benzyl-6-(ethylamino)-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NCC)S(=O)(=N)CCC QNJDNDBLKCNKGH-UHFFFAOYSA-N 0.000 claims description 2
- YSCLHWJXXFOWHI-UHFFFAOYSA-N 9-benzyl-6-(propan-2-ylamino)-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NC(C)C)S(=O)(=N)CCC YSCLHWJXXFOWHI-UHFFFAOYSA-N 0.000 claims description 2
- QXOBPBVKQCQQAI-UHFFFAOYSA-N 9-benzyl-6-(propylamino)-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NCCC)S(=O)(=N)CCC QXOBPBVKQCQQAI-UHFFFAOYSA-N 0.000 claims description 2
- MSSXPOADQWRGGF-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-(propylsulfonimidoyl)-7H-purin-6-yl]-2,2-dimethylpropanamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C(C)(C)C)=O)S(=O)(=N)CCC MSSXPOADQWRGGF-UHFFFAOYSA-N 0.000 claims description 2
- OCLKTSCMYMCMJQ-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-(propylsulfonimidoyl)-7H-purin-6-yl]-2-ethylbutanamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C(CC)CC)=O)S(=O)(=N)CCC OCLKTSCMYMCMJQ-UHFFFAOYSA-N 0.000 claims description 2
- ZKJRMYURRTVASS-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-(propylsulfonimidoyl)-7H-purin-6-yl]-2-methylpentanamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C(CCC)C)=O)S(=O)(=N)CCC ZKJRMYURRTVASS-UHFFFAOYSA-N 0.000 claims description 2
- GBEBBMFAEQUXKE-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-(propylsulfonimidoyl)-7H-purin-6-yl]-2-propylpentanamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C(CCC)CCC)=O)S(=O)(=N)CCC GBEBBMFAEQUXKE-UHFFFAOYSA-N 0.000 claims description 2
- YJXYKDUWIFDOMI-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-(propylsulfonimidoyl)-7H-purin-6-yl]-3-methylbutanamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(CC(C)C)=O)S(=O)(=N)CCC YJXYKDUWIFDOMI-UHFFFAOYSA-N 0.000 claims description 2
- OSSHGUPKKOUUGT-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-(propylsulfonimidoyl)-7H-purin-6-yl]acetamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C)=O)S(=O)(=N)CCC OSSHGUPKKOUUGT-UHFFFAOYSA-N 0.000 claims description 2
- PQNPXVINORKDLR-UHFFFAOYSA-N N-[9-benzyl-8-oxo-2-(propylsulfonimidoyl)-7H-purin-6-yl]-2-propylpentanamide Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NC(C(CCC)CCC)=O)S(=O)(=N)CCC PQNPXVINORKDLR-UHFFFAOYSA-N 0.000 claims description 2
- BCXKQQHBMBXTLH-UHFFFAOYSA-N N-[9-benzyl-8-oxo-2-(propylsulfonimidoyl)-7H-purin-6-yl]pentanamide Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NC(CCCC)=O)S(=O)(=N)CCC BCXKQQHBMBXTLH-UHFFFAOYSA-N 0.000 claims description 2
- VWICUQQUYQWFGE-UHFFFAOYSA-N [6-amino-9-benzyl-2-(methylsulfonimidoyl)-8-oxopurin-7-yl]methyl acetate Chemical compound C(C)(=O)OCN1C(N(C2=NC(=NC(=C12)N)S(=O)(=N)C)CC1=CC=CC=C1)=O VWICUQQUYQWFGE-UHFFFAOYSA-N 0.000 claims description 2
- OEOSDGACEVTXNN-UHFFFAOYSA-N [6-amino-9-benzyl-8-oxo-2-(propylsulfonimidoyl)purin-7-yl]methyl acetate Chemical compound C(C)(=O)OCN1C(N(C2=NC(=NC(=C12)N)S(=O)(=N)CCC)CC1=CC=CC=C1)=O OEOSDGACEVTXNN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004543 purin-7-yl group Chemical group N1=CN=C2N=CN(C2=C1)* 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 9
- 125000004803 chlorobenzyl group Chemical group 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 8
- 125000006178 methyl benzyl group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 125000004175 fluorobenzyl group Chemical group 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 239000003153 chemical reaction reagent Substances 0.000 claims 4
- 125000002946 cyanobenzyl group Chemical group 0.000 claims 4
- 125000006287 difluorobenzyl group Chemical group 0.000 claims 4
- 208000002672 hepatitis B Diseases 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
- BRSQFEYCEJEYCJ-UHFFFAOYSA-N 6-amino-2-(ethylsulfonimidoyl)-9-[(4-methylphenyl)methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CC)CC1=CC=C(C=C1)C)=O BRSQFEYCEJEYCJ-UHFFFAOYSA-N 0.000 claims 3
- UTHROXJUYVNHHL-DEOSSOPVSA-N 6-amino-9-[(4-chlorophenyl)methyl]-2-(ethylsulfonimidoyl)-7H-purin-8-one Chemical compound CC[S@](=N)(=O)C1=NC(N)=C2NC(=O)N(CC3=CC=C(Cl)C=C3)C2=N1 UTHROXJUYVNHHL-DEOSSOPVSA-N 0.000 claims 3
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- LUXRVHGJZAYSCL-UHFFFAOYSA-N 4-[[6-amino-8-oxo-2-(propylsulfonimidoyl)-7H-purin-9-yl]methyl]benzoic acid Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC=C(C(=O)O)C=C1)=O LUXRVHGJZAYSCL-UHFFFAOYSA-N 0.000 claims 2
- GVKDJOFFPHLPOW-UHFFFAOYSA-N 6-amino-9-[(4-bromophenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC=C(C=C1)Br)=O GVKDJOFFPHLPOW-UHFFFAOYSA-N 0.000 claims 2
- WLAWDJREXFPHPH-VWLOTQADSA-N 6-amino-9-[(4-chlorophenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound C(C1=CC=C(Cl)C=C1)N1C2=C(C(=NC([S@](=O)(=N)CCC)=N2)N)NC1=O WLAWDJREXFPHPH-VWLOTQADSA-N 0.000 claims 2
- OZGLMHHFCJLROC-UHFFFAOYSA-N 6-amino-9-[(4-fluorophenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC=C(C=C1)F)=O OZGLMHHFCJLROC-UHFFFAOYSA-N 0.000 claims 2
- YXFJJQUVGAPZKB-UHFFFAOYSA-N 6-amino-9-[(4-methylphenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC=C(C=C1)C)=O YXFJJQUVGAPZKB-UHFFFAOYSA-N 0.000 claims 2
- OMOVBYAITFNLQV-UHFFFAOYSA-N 6-amino-9-[(6-chloropyridin-3-yl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC=1C=NC(=CC=1)Cl)=O OMOVBYAITFNLQV-UHFFFAOYSA-N 0.000 claims 2
- BQGJLGCRAYYVSZ-UHFFFAOYSA-N 6-amino-9-[(6-methylpyridin-3-yl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC=1C=NC(=CC=1)C)=O BQGJLGCRAYYVSZ-UHFFFAOYSA-N 0.000 claims 2
- KFDGFNQIYSAVAY-UHFFFAOYSA-N 6-amino-9-benzyl-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC=CC=C1)=O KFDGFNQIYSAVAY-UHFFFAOYSA-N 0.000 claims 2
- CARHRXYETPUULC-UHFFFAOYSA-N 6-methyl-9-[(2-methylpyrimidin-5-yl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound CC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC=1C=NC(=NC=1)C)=O CARHRXYETPUULC-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000006278 bromobenzyl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000006286 dichlorobenzyl group Chemical group 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- GJWKQSSMTVBHRA-UHFFFAOYSA-N methyl 4-[[6-amino-8-oxo-2-(propylsulfonimidoyl)-7H-purin-9-yl]methyl]benzoate Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC=C(C(=O)OC)C=C1)=O GJWKQSSMTVBHRA-UHFFFAOYSA-N 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims 2
- MRIWBJKYLHNMRZ-UHFFFAOYSA-N 3-[[6-amino-8-oxo-2-(propylsulfonimidoyl)-7H-purin-9-yl]methyl]benzamide Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC=1C=C(C(=O)N)C=CC=1)=O MRIWBJKYLHNMRZ-UHFFFAOYSA-N 0.000 claims 1
- HMLYDPXOOQGKTP-UHFFFAOYSA-N 3-[[6-amino-8-oxo-2-(propylsulfonimidoyl)-7H-purin-9-yl]methyl]benzonitrile Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC=1C=C(C#N)C=CC=1)=O HMLYDPXOOQGKTP-UHFFFAOYSA-N 0.000 claims 1
- XEIFQSWWZYZIMI-UHFFFAOYSA-N 4-[[6-amino-8-oxo-2-(propylsulfonimidoyl)-7H-purin-9-yl]methyl]-N-(2-methoxyethyl)benzamide Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC=C(C(=O)NCCOC)C=C1)=O XEIFQSWWZYZIMI-UHFFFAOYSA-N 0.000 claims 1
- YUCCBADIVGNCIC-UHFFFAOYSA-N 4-[[6-amino-8-oxo-2-(propylsulfonimidoyl)-7H-purin-9-yl]methyl]benzamide Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC=C(C(=O)N)C=C1)=O YUCCBADIVGNCIC-UHFFFAOYSA-N 0.000 claims 1
- OOTVBBLVGZVFGS-UHFFFAOYSA-N 4-[[6-amino-8-oxo-2-(propylsulfonimidoyl)-7H-purin-9-yl]methyl]benzonitrile Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC=C(C#N)C=C1)=O OOTVBBLVGZVFGS-UHFFFAOYSA-N 0.000 claims 1
- MJRDPVUQHOCHAV-UHFFFAOYSA-N 6-amino-2-(3-chloropropylsulfonimidoyl)-9-[(4-methoxyphenyl)methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCCCl)CC1=CC=C(C=C1)OC)=O MJRDPVUQHOCHAV-UHFFFAOYSA-N 0.000 claims 1
- UOCHSLAWCBRFAO-UHFFFAOYSA-N 6-amino-2-(ethylsulfonimidoyl)-9-[(4-fluorophenyl)methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CC)CC1=CC=C(C=C1)F)=O UOCHSLAWCBRFAO-UHFFFAOYSA-N 0.000 claims 1
- WJVVXYFIAALPNG-UHFFFAOYSA-N 6-amino-2-(methylsulfonimidoyl)-9-(pyridin-2-ylmethyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)C)CC1=NC=CC=C1)=O WJVVXYFIAALPNG-UHFFFAOYSA-N 0.000 claims 1
- MSSWBOIWSSIBHI-UHFFFAOYSA-N 6-amino-2-(methylsulfonimidoyl)-9-(pyridin-3-ylmethyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)C)CC=1C=NC=CC=1)=O MSSWBOIWSSIBHI-UHFFFAOYSA-N 0.000 claims 1
- GMEXKXFTVMLTOL-UHFFFAOYSA-N 6-amino-2-(methylsulfonimidoyl)-9-(pyridin-4-ylmethyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)C)CC1=CC=NC=C1)=O GMEXKXFTVMLTOL-UHFFFAOYSA-N 0.000 claims 1
- ZUOHLJLBZUSZLB-UHFFFAOYSA-N 6-amino-2-(propylsulfonimidoyl)-9-[[4-(pyrrolidine-1-carbonyl)phenyl]methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC=C(C=C1)C(=O)N1CCCC1)=O ZUOHLJLBZUSZLB-UHFFFAOYSA-N 0.000 claims 1
- APBICSQRGKTYKB-UHFFFAOYSA-N 6-amino-2-(propylsulfonimidoyl)-9-[[4-(trifluoromethyl)phenyl]methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC=C(C=C1)C(F)(F)F)=O APBICSQRGKTYKB-UHFFFAOYSA-N 0.000 claims 1
- YEPVOOTXMQFLJF-UHFFFAOYSA-N 6-amino-9-(2-methylpropyl)-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC(C)C)=O YEPVOOTXMQFLJF-UHFFFAOYSA-N 0.000 claims 1
- OYDTTXSWKNTOFY-UHFFFAOYSA-N 6-amino-9-[(2,4-difluorophenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=C(C=C(C=C1)F)F)=O OYDTTXSWKNTOFY-UHFFFAOYSA-N 0.000 claims 1
- KZXZEGLHTOJPOP-UHFFFAOYSA-N 6-amino-9-[(2-chlorophenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=C(C=CC=C1)Cl)=O KZXZEGLHTOJPOP-UHFFFAOYSA-N 0.000 claims 1
- GHNZGJFSLUTYGY-UHFFFAOYSA-N 6-amino-9-[(2-methylpyridin-4-yl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC(=NC=C1)C)=O GHNZGJFSLUTYGY-UHFFFAOYSA-N 0.000 claims 1
- MBQBYGUMANOLRF-UHFFFAOYSA-N 6-amino-9-[(3,4-dichlorophenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC(=C(C=C1)Cl)Cl)=O MBQBYGUMANOLRF-UHFFFAOYSA-N 0.000 claims 1
- JXBUDGCMKVLNEW-UHFFFAOYSA-N 6-amino-9-[(3,4-difluorophenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC(=C(C=C1)F)F)=O JXBUDGCMKVLNEW-UHFFFAOYSA-N 0.000 claims 1
- YNGIHTJQHZVVFN-UHFFFAOYSA-N 6-amino-9-[(3-chloro-4-methylphenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC(=C(C=C1)C)Cl)=O YNGIHTJQHZVVFN-UHFFFAOYSA-N 0.000 claims 1
- FQRMTGZFXMHCSC-UHFFFAOYSA-N 6-amino-9-[(3-chlorophenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC(=CC=C1)Cl)=O FQRMTGZFXMHCSC-UHFFFAOYSA-N 0.000 claims 1
- RXVPTJHAOBJTOO-UHFFFAOYSA-N 6-amino-9-[(4-chloro-3-fluorophenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC(=C(C=C1)Cl)F)=O RXVPTJHAOBJTOO-UHFFFAOYSA-N 0.000 claims 1
- IYZZWMCSHFSKJC-UHFFFAOYSA-N 6-amino-9-[(4-chloro-3-methylphenyl)methyl]-2-(propylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC1=CC(=C(C=C1)Cl)C)=O IYZZWMCSHFSKJC-UHFFFAOYSA-N 0.000 claims 1
- YOKSITUASXLPJK-UHFFFAOYSA-N 6-amino-9-[(4-chlorophenyl)methyl]-2-(methylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)C)CC1=CC=C(C=C1)Cl)=O YOKSITUASXLPJK-UHFFFAOYSA-N 0.000 claims 1
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| PCT/EP2016/059961 WO2016180695A1 (en) | 2015-05-08 | 2016-05-04 | Novel sulfonimidoylpurinone compounds and derivatives for the treatment and prophylaxis of virus infection |
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| NZ735648A (en) | 2015-05-08 | 2023-06-30 | Hoffmann La Roche | Novel sulfonimidoylpurinone compounds and derivatives for the treatment and prophylaxis of virus infection |
| SG11201901633WA (en) | 2016-08-29 | 2019-03-28 | Hoffmann La Roche | 7-substituted sulfonimidoylpurinone compounds for the treatment and prophylaxis of virus infection |
| WO2018050571A1 (en) * | 2016-09-13 | 2018-03-22 | F. Hoffmann-La Roche Ag | Combined treatment with a tlr7 agonist and an hbv capsid assembly inhibitor |
| EP3752505B1 (en) | 2018-02-12 | 2023-01-11 | F. Hoffmann-La Roche AG | Novel sulfone compounds and derivatives for the treatment and prophylaxis of virus infection |
| CA3091950A1 (en) * | 2018-02-28 | 2019-09-06 | F. Hoffmann-La Roche Ag | 7-substituted sulfonimidoylpurinone compounds and derivatives for the treatment and prophylaxis of liver cancer |
| CN111072667A (zh) * | 2018-10-22 | 2020-04-28 | 罗欣药业(上海)有限公司 | 五元或六元杂环并嘧啶类化合物及其用途 |
| CN119455003A (zh) * | 2019-02-12 | 2025-02-18 | Ambrx公司 | 包含抗体-tlr激动剂缀合物的组合物、方法和用途 |
| CN114450280B (zh) | 2019-09-20 | 2025-02-25 | 先正达农作物保护股份公司 | 具有含硫和亚砜亚胺取代基的杀有害生物活性杂环衍生物 |
| US20230131192A1 (en) * | 2020-01-27 | 2023-04-27 | Bristol-Myers Squibb Company | 1H-PYRAZOLO[4,3-d]PYRIMIDINE COMPOUNDS AS TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS |
| KR20220132590A (ko) * | 2020-01-27 | 2022-09-30 | 브리스톨-마이어스 스큅 컴퍼니 | 톨-유사 수용체 7 (TLR7) 효능제로서의 1H-피라졸로[4,3-d]피리미딘 화합물 |
| WO2024013205A1 (en) | 2022-07-14 | 2024-01-18 | F. Hoffmann-La Roche Ag | Phosphorylpurinone compounds for the treatment of cancer |
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| JP2008540396A (ja) * | 2005-05-04 | 2008-11-20 | ファイザー・リミテッド | 癌およびｃ型肝炎などのウイルス感染を治療するためのトール様受容体調節薬としての２−アミド−６−アミノ−８−オキソプリン誘導体 |
| CN101239980B (zh) | 2008-02-18 | 2011-06-22 | 靳广毅 | 免疫受体调节剂偶联体前体和偶联体及其应用 |
| PE20120106A1 (es) | 2008-12-09 | 2012-02-20 | Gilead Sciences Inc | Moduladores de receptores tipo toll |
| WO2011079016A1 (en) | 2009-12-22 | 2011-06-30 | Gilead Sciences, Inc. | Methods of treating hbv and hcv infection |
| TWI555737B (zh) | 2011-05-24 | 2016-11-01 | 拜耳知識產權公司 | 含有硫醯亞胺基團之４－芳基－ｎ－苯基－１，３，５－三氮雜苯－２－胺 |
| JP6349256B2 (ja) | 2011-11-09 | 2018-06-27 | ヤンセン・サイエンシズ・アイルランド・ユーシー | ウイルス感染の治療のためのプリン誘導体 |
| PL2978429T3 (pl) | 2013-03-29 | 2017-08-31 | Janssen Sciences Ireland Uc | Deazapurynony makrocykliczne do leczenia infekcji wirusowych |
| BR112017002811B1 (pt) | 2014-08-15 | 2022-09-06 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Compostos de pirrolopirimidina usados como agonista de tlr7 e seu uso, composição farmacêutica e kit |
| NZ735648A (en) * | 2015-05-08 | 2023-06-30 | Hoffmann La Roche | Novel sulfonimidoylpurinone compounds and derivatives for the treatment and prophylaxis of virus infection |
| SG11201901633WA (en) * | 2016-08-29 | 2019-03-28 | Hoffmann La Roche | 7-substituted sulfonimidoylpurinone compounds for the treatment and prophylaxis of virus infection |
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