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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- XVAXOGSGLHCPMT-UHFFFAOYSA-N 6-amino-9-benzyl-2-(2-methoxyethylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCOC)CC1=CC=CC=C1)=O XVAXOGSGLHCPMT-UHFFFAOYSA-N 0.000 claims 1
- CDMVZHHOTBQWJC-UHFFFAOYSA-N 6-amino-9-benzyl-2-(3-methoxypropylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCCOC)CC1=CC=CC=C1)=O CDMVZHHOTBQWJC-UHFFFAOYSA-N 0.000 claims 1
- LANQXZNXIDTWRX-UHFFFAOYSA-N 6-amino-9-benzyl-2-(butylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCCC)CC1=CC=CC=C1)=O LANQXZNXIDTWRX-UHFFFAOYSA-N 0.000 claims 1
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- XFDVJIPIVPRMJX-UHFFFAOYSA-N 6-amino-9-benzyl-2-(ethylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CC)CC1=CC=CC=C1)=O XFDVJIPIVPRMJX-UHFFFAOYSA-N 0.000 claims 1
- GJZZDPHTUXZRDP-UHFFFAOYSA-N 6-amino-9-benzyl-2-(methylsulfonimidoyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)(=N)C)CC1=CC=CC=C1)=O GJZZDPHTUXZRDP-UHFFFAOYSA-N 0.000 claims 1
- WJLOTTAIZSVTCY-UHFFFAOYSA-N 6-methyl-2-(propylsulfonimidoyl)-9-(pyrimidin-5-ylmethyl)-7H-purin-8-one Chemical compound CC1=C2NC(N(C2=NC(=N1)S(=O)(=N)CCC)CC=1C=NC=NC=1)=O WJLOTTAIZSVTCY-UHFFFAOYSA-N 0.000 claims 1
- 102000006992 Interferon-alpha Human genes 0.000 claims 1
- 108010047761 Interferon-alpha Proteins 0.000 claims 1
- 239000013543 active substance Substances 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
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000006393 methylpyrimidinyl group Chemical group 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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| PL3294740T3 (pl) | 2015-05-08 | 2020-03-31 | F. Hoffmann-La Roche Ag | Nowe sulfonoimidoilopurynony i pochodne do leczenia i profilaktyki infekcji wirusowych |
| PL3504210T3 (pl) * | 2016-08-29 | 2021-07-05 | F. Hoffmann-La Roche Ag | 7-podstawione związki sulfonimidoilopurynonowe do leczenia i profilaktyki zakażeń wirusowych |
| EP3512556B1 (en) | 2016-09-13 | 2021-08-18 | F. Hoffmann-La Roche AG | Combined treatment with a tlr7 agonist and an hbv capsid assembly inhibitor |
| JP7328977B2 (ja) | 2018-02-12 | 2023-08-17 | エフ． ホフマン－ラ ロシュ アーゲー | ウイルス感染の処置および予防のための新規のスルホン化合物および誘導体 |
| JP7089596B2 (ja) * | 2018-02-28 | 2022-06-22 | エフ・ホフマン－ラ・ロシュ・アクチェンゲゼルシャフト | 肝がんの治療及び予防のための７位置換スルホンイミドイルプリノン化合物及び誘導体 |
| 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 |
| CA3128081A1 (en) * | 2019-02-12 | 2020-08-20 | Ambrx, Inc. | Compositions containing, methods and uses of antibody-tlr agonist conjugates |
| US12503461B2 (en) | 2019-09-20 | 2025-12-23 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur and sulfoximine containing substituents |
| WO2021154662A1 (en) * | 2020-01-27 | 2021-08-05 | Bristol-Myers Squibb Company | 1H-PYRAZOLO[4,3-d]PYRIMIDINE COMPOUNDS AS TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS |
| EP4097105A1 (en) * | 2020-01-27 | 2022-12-07 | Bristol-Myers Squibb Company | 1h-pyrazolo[4,3-d]pyrimidine compounds as toll-like receptor 7 (tlr7) agonists |
| EP4554678A1 (en) | 2022-07-14 | 2025-05-21 | F. Hoffmann-La Roche AG | Phosphorylpurinone compounds for the treatment of cancer |
| CN118724963A (zh) * | 2023-03-30 | 2024-10-01 | 浙江养生堂天然药物研究所有限公司 | 含磷或含硫的大环化合物及其用途 |
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| JP4189048B2 (ja) * | 1997-12-26 | 2008-12-03 | 大日本住友製薬株式会社 | 複素環化合物 |
| AU2006242920A1 (en) * | 2005-05-04 | 2006-11-09 | Pfizer Limited | 2-amido-6-amino-8-oxopurine derivatives as Toll-Like receptor modulators for the treatment of cancer and viral infections, such as hepatitis C |
| 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 |
| RS53347B (sr) * | 2008-12-09 | 2014-10-31 | Gilead Sciences, Inc. | Modulatori toll-sličnih receptora |
| US20110150836A1 (en) | 2009-12-22 | 2011-06-23 | 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 |
| CN110590809B (zh) | 2013-03-29 | 2022-04-19 | 爱尔兰詹森科学公司 | 用于治疗病毒感染的大环脱氮-嘌呤酮 |
| HRP20210927T1 (hr) | 2014-08-15 | 2021-09-03 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Spojevi pirolopirimidina koje se koriste kao agonist tlr7 |
| PL3294740T3 (pl) * | 2015-05-08 | 2020-03-31 | F. Hoffmann-La Roche Ag | Nowe sulfonoimidoilopurynony i pochodne do leczenia i profilaktyki infekcji wirusowych |
| PL3504210T3 (pl) * | 2016-08-29 | 2021-07-05 | F. Hoffmann-La Roche Ag | 7-podstawione związki sulfonimidoilopurynonowe do leczenia i profilaktyki zakażeń wirusowych |
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