JPWO2020023710A5 - - Google Patents
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- Publication number
- JPWO2020023710A5 JPWO2020023710A5 JP2021504466A JP2021504466A JPWO2020023710A5 JP WO2020023710 A5 JPWO2020023710 A5 JP WO2020023710A5 JP 2021504466 A JP2021504466 A JP 2021504466A JP 2021504466 A JP2021504466 A JP 2021504466A JP WO2020023710 A5 JPWO2020023710 A5 JP WO2020023710A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- fluorophenyl
- chloro
- carbamoyl
- carbamate
- 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 C 1 -C 6 alkyl Chemical group 0.000 claims 58
- 239000003795 chemical substances by application Substances 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 241000700721 Hepatitis B virus Species 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 208000037262 Hepatitis delta Diseases 0.000 claims 7
- 241000724709 Hepatitis delta virus Species 0.000 claims 7
- 208000015181 infectious disease Diseases 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 230000008685 targeting Effects 0.000 claims 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 3
- 108091036055 CccDNA Proteins 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 229940124765 capsid inhibitor Drugs 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 230000000368 destabilizing effect Effects 0.000 claims 3
- 230000003308 immunostimulating effect Effects 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 239000002773 nucleotide Substances 0.000 claims 3
- 125000003729 nucleotide group Chemical group 0.000 claims 3
- 108090000623 proteins and genes Proteins 0.000 claims 3
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 2
- OVRNDRQMDRJTHS-KEWYIRBNSA-N N-acetyl-D-galactosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-KEWYIRBNSA-N 0.000 claims 2
- MBLBDJOUHNCFQT-UHFFFAOYSA-N N-acetyl-D-galactosamine Natural products CC(=O)NC(C=O)C(O)C(O)C(O)CO MBLBDJOUHNCFQT-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 208000006454 hepatitis Diseases 0.000 claims 2
- 231100000283 hepatitis Toxicity 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- LDNSHTVNGGHGQJ-UHFFFAOYSA-N pyrrole-1-carboxamide Chemical compound NC(=O)N1C=CC=C1 LDNSHTVNGGHGQJ-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- VTYSFMVKDRKRCT-UHFFFAOYSA-N (1-methyl-1,2,4-triazol-3-yl)methyl N-[3-[[2-(difluoromethyl)pyridin-4-yl]carbamoyl]-2-methyl-5,6-dihydro-4H-cyclopenta[c]pyrrol-6-yl]carbamate Chemical compound FC(C1=NC=CC(=C1)NC(=O)C=1N(C=C2C=1CCC2NC(OCC1=NN(C=N1)C)=O)C)F VTYSFMVKDRKRCT-UHFFFAOYSA-N 0.000 claims 1
- CBYKQBNVZOPCSB-UHFFFAOYSA-N (1-methyltriazol-4-yl)methyl N-[3-[(3-chloro-4-fluorophenyl)carbamoyl]-2-methyl-5,6-dihydro-4H-cyclopenta[c]pyrrol-6-yl]carbamate Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(OCC=1N=NN(C=1)C)=O)C CBYKQBNVZOPCSB-UHFFFAOYSA-N 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- CBPSICKQSVJOID-UHFFFAOYSA-N 1,3-oxazol-2-ylmethyl N-[3-[(3-chloro-4-fluorophenyl)carbamoyl]-2-methyl-5,6-dihydro-4H-cyclopenta[c]pyrrol-6-yl]carbamate Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(OCC=1OC=CN=1)=O)C CBPSICKQSVJOID-UHFFFAOYSA-N 0.000 claims 1
- OKBSFHXJFATRNP-UHFFFAOYSA-N 1,3-oxazol-5-ylmethyl N-[3-[(3-chloro-4-fluorophenyl)carbamoyl]-2-methyl-5,6-dihydro-4H-cyclopenta[c]pyrrol-6-yl]carbamate Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(OCC1=CN=CO1)=O)C OKBSFHXJFATRNP-UHFFFAOYSA-N 0.000 claims 1
- HHIAIUUYWNGBMR-UHFFFAOYSA-N 1-[[3-[(3-chloro-4-fluorophenyl)carbamoyl]-2-methyl-5,6-dihydro-4H-cyclopenta[c]pyrrol-6-yl]carbamoyloxymethyl]-3,3-difluorocyclobutane-1-carboxylic acid Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(=O)OCC1(CC(C1)(F)F)C(=O)O)C HHIAIUUYWNGBMR-UHFFFAOYSA-N 0.000 claims 1
- SPCHACUESSVRGE-UHFFFAOYSA-N 1H-1,2,4-triazol-5-ylmethyl N-[3-[(3-chloro-4-fluorophenyl)carbamoyl]-1-cyclopropyl-2-methyl-5,6-dihydro-4H-cyclopenta[c]pyrrol-6-yl]carbamate Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C(=C2C=1CCC2NC(OCC1=NNC=N1)=O)C1CC1)C SPCHACUESSVRGE-UHFFFAOYSA-N 0.000 claims 1
- XQYAVNYXYHOUIS-UHFFFAOYSA-N 2-cyanoethyl N-[3-[(3-chloro-4-fluorophenyl)carbamoyl]-2-methyl-5,6-dihydro-4H-cyclopenta[c]pyrrol-6-yl]carbamate Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(OCCC#N)=O)C XQYAVNYXYHOUIS-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- WVRVQZBSXNQNDQ-UHFFFAOYSA-N 2H-triazol-4-ylmethyl N-[3-[(3-chloro-4-fluorophenyl)carbamoyl]-1,2-dimethyl-5,6-dihydro-4H-cyclopenta[c]pyrrol-6-yl]carbamate Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C(=C2C=1CCC2NC(OCC=1N=NNC=1)=O)C)C WVRVQZBSXNQNDQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- GMMXJGLTDJCHNR-UHFFFAOYSA-N 4-amino-N-(3-chloro-4-fluorophenyl)-2-methyl-5,6,7,8-tetrahydro-4H-cyclohepta[c]pyrrole-1-carboxamide Chemical compound NC1CCCCC2=C(N(C=C21)C)C(=O)NC1=CC(=C(C=C1)F)Cl GMMXJGLTDJCHNR-UHFFFAOYSA-N 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- PPOBQVRYFRVLOP-UHFFFAOYSA-N 6-amino-N-(3-chloro-4-fluorophenyl)-2-methyl-5,6-dihydro-4H-cyclopenta[c]pyrrole-3-carboxamide Chemical compound NC1CCC2=C(N(C=C21)C)C(=O)NC1=CC(=C(C=C1)F)Cl PPOBQVRYFRVLOP-UHFFFAOYSA-N 0.000 claims 1
- JIJFLJLOGPUXMI-UHFFFAOYSA-N BrC1=C2C(=C(N1C)C(NC1=CC(=C(C=C1)F)Cl)=O)CCC2NC(OCC1=NN(C=N1)C)=O Chemical compound BrC1=C2C(=C(N1C)C(NC1=CC(=C(C=C1)F)Cl)=O)CCC2NC(OCC1=NN(C=N1)C)=O JIJFLJLOGPUXMI-UHFFFAOYSA-N 0.000 claims 1
- ZACGMNWVDJOGDJ-UHFFFAOYSA-N BrC1=C2C(=C(N1C)C(NC1=CC(=C(C=C1)F)Cl)=O)CCC2NC(OCC1=NNC=N1)=O Chemical compound BrC1=C2C(=C(N1C)C(NC1=CC(=C(C=C1)F)Cl)=O)CCC2NC(OCC1=NNC=N1)=O ZACGMNWVDJOGDJ-UHFFFAOYSA-N 0.000 claims 1
- OGMKQQISLVRSKV-UHFFFAOYSA-N C(#N)C=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(OCC1=NN(C=N1)C)=O)C Chemical compound C(#N)C=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(OCC1=NN(C=N1)C)=O)C OGMKQQISLVRSKV-UHFFFAOYSA-N 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- GPIYQDHHUYJILX-UHFFFAOYSA-N CN1C(=C2C(=C1)C(CC2)NC(OCC1=NN(C=N1)C)=O)C(NC1=CC(=C(C(=C1)F)F)F)=O Chemical compound CN1C(=C2C(=C1)C(CC2)NC(OCC1=NN(C=N1)C)=O)C(NC1=CC(=C(C(=C1)F)F)F)=O GPIYQDHHUYJILX-UHFFFAOYSA-N 0.000 claims 1
- LOWQORFIQUZUCB-UHFFFAOYSA-N CN1C(=C2C(=C1)C(CC2)NC(OCC1=NN(C=N1)C)=O)C(NC1=CC(=NC=C1)C(F)(F)F)=O Chemical compound CN1C(=C2C(=C1)C(CC2)NC(OCC1=NN(C=N1)C)=O)C(NC1=CC(=NC=C1)C(F)(F)F)=O LOWQORFIQUZUCB-UHFFFAOYSA-N 0.000 claims 1
- 108090000565 Capsid Proteins Proteins 0.000 claims 1
- 102100023321 Ceruloplasmin Human genes 0.000 claims 1
- TXMQCIAXLOWUQX-UHFFFAOYSA-N ClC1=C2C(=C(N1C)C(NC1=CC(=C(C=C1)F)Cl)=O)CCC2NC(OCC1=NN(C=N1)C)=O Chemical compound ClC1=C2C(=C(N1C)C(NC1=CC(=C(C=C1)F)Cl)=O)CCC2NC(OCC1=NN(C=N1)C)=O TXMQCIAXLOWUQX-UHFFFAOYSA-N 0.000 claims 1
- KIRMPMWYENLLJR-UHFFFAOYSA-N ClC1=C2C(=C(N1C)C(NC1=CC(=C(C=C1)F)Cl)=O)CCC2NC(OCC1=NNC=N1)=O Chemical compound ClC1=C2C(=C(N1C)C(NC1=CC(=C(C=C1)F)Cl)=O)CCC2NC(OCC1=NNC=N1)=O KIRMPMWYENLLJR-UHFFFAOYSA-N 0.000 claims 1
- GVFXAWPESNECDM-UHFFFAOYSA-N ClC1=C2C(=C(N1C)C(NC1=CC(=C(C=C1)F)Cl)=O)CCC2NC(OCC1=NNN=C1)=O Chemical compound ClC1=C2C(=C(N1C)C(NC1=CC(=C(C=C1)F)Cl)=O)CCC2NC(OCC1=NNN=C1)=O GVFXAWPESNECDM-UHFFFAOYSA-N 0.000 claims 1
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- GECHFLOIDIPSAR-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NS(=O)(=O)C1CC1)C Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NS(=O)(=O)C1CC1)C GECHFLOIDIPSAR-UHFFFAOYSA-N 0.000 claims 1
- BXKVCCKSMCSDQH-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCCCC2NC(OC)=O)C Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCCCC2NC(OC)=O)C BXKVCCKSMCSDQH-UHFFFAOYSA-N 0.000 claims 1
- HEFYOBUAXNEARI-UHFFFAOYSA-N ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCCCC2NC(OCC1=NN(C=N1)C)=O)C Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCCCC2NC(OCC1=NN(C=N1)C)=O)C HEFYOBUAXNEARI-UHFFFAOYSA-N 0.000 claims 1
- UPZGWPGKFLZSON-UHFFFAOYSA-N ClC=1N(C(=C2CCCC(C=12)NC(OCC1=NN(C=N1)C)=O)C(NC1=CC(=C(C=C1)F)Cl)=O)C Chemical compound ClC=1N(C(=C2CCCC(C=12)NC(OCC1=NN(C=N1)C)=O)C(NC1=CC(=C(C=C1)F)Cl)=O)C UPZGWPGKFLZSON-UHFFFAOYSA-N 0.000 claims 1
- WLTUXKPECGXJSE-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(OCC1=NN(C=N1)C)=O)C)F Chemical compound FC(C=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(OCC1=NN(C=N1)C)=O)C)F WLTUXKPECGXJSE-UHFFFAOYSA-N 0.000 claims 1
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- KFHLEGHOHXMTMW-UHFFFAOYSA-N FC1=C(C=C(C=C1)NC(=O)C=1N(C=C2C=1CCC2NC(OCC1=NN(C=N1)C)=O)C)C(F)(F)F Chemical compound FC1=C(C=C(C=C1)NC(=O)C=1N(C=C2C=1CCC2NC(OCC1=NN(C=N1)C)=O)C)C(F)(F)F KFHLEGHOHXMTMW-UHFFFAOYSA-N 0.000 claims 1
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- HCXNUYMYSQXSIU-UHFFFAOYSA-N methyl N-[3-[(3-chloro-4-fluorophenyl)carbamoyl]-2-methyl-5,6-dihydro-4H-cyclopenta[c]pyrrol-6-yl]carbamate Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(OC)=O)C HCXNUYMYSQXSIU-UHFFFAOYSA-N 0.000 claims 1
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- WRPDZQNEPZZSJG-UHFFFAOYSA-N propan-2-yl 1-[[3-[(3-chloro-4-fluorophenyl)carbamoyl]-2-methyl-5,6-dihydro-4H-cyclopenta[c]pyrrol-6-yl]carbamoyloxymethyl]-3,3-difluorocyclobutane-1-carboxylate Chemical compound ClC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(=O)OCC1(CC(C1)(F)F)C(=O)OC(C)C)C WRPDZQNEPZZSJG-UHFFFAOYSA-N 0.000 claims 1
- MTNAGZWSAVGYDX-UHFFFAOYSA-N pyridin-2-ylmethyl N-[3-[(3,4-difluorophenyl)carbamoyl]-2-methyl-5,6-dihydro-4H-cyclopenta[c]pyrrol-6-yl]carbamate Chemical compound FC=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CCC2NC(OCC1=NC=CC=C1)=O)C MTNAGZWSAVGYDX-UHFFFAOYSA-N 0.000 claims 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
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| US20220055989A1 (en) * | 2018-12-21 | 2022-02-24 | Albert Ludwing Universität Freiburg | Condensed pyrroles as novel bromodomain inhibitors |
| TW202214585A (zh) * | 2020-06-08 | 2022-04-16 | 加拿大商愛彼特生物製藥公司 | 經取代之異喹啉基甲基醯胺類、其類似物及使用其之方法 |
| KR102559870B1 (ko) * | 2021-04-27 | 2023-07-26 | 주식회사 켐얼라이언스 | 카르밤산염 화합물의 제조방법 |
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- 2019-07-25 WO PCT/US2019/043373 patent/WO2020023710A1/en not_active Ceased
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- 2019-07-25 AU AU2019309852A patent/AU2019309852B2/en not_active Expired - Fee Related
- 2019-07-25 CN CN201980057464.7A patent/CN112638376B/zh active Active
- 2019-07-25 EP EP19842210.7A patent/EP3829570A4/en not_active Withdrawn
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- 2019-07-25 KR KR1020217005889A patent/KR20210039417A/ko not_active Ceased
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2024
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