JP2016509591A5 - - Google Patents
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- JP2016509591A5 JP2016509591A5 JP2015550788A JP2015550788A JP2016509591A5 JP 2016509591 A5 JP2016509591 A5 JP 2016509591A5 JP 2015550788 A JP2015550788 A JP 2015550788A JP 2015550788 A JP2015550788 A JP 2015550788A JP 2016509591 A5 JP2016509591 A5 JP 2016509591A5
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- JP
- Japan
- Prior art keywords
- optionally substituted
- diastereomer
- compound
- enantiomer
- acceptable salt
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims description 168
- 150000001875 compounds Chemical class 0.000 claims description 133
- 150000003839 salts Chemical class 0.000 claims description 116
- 229910052739 hydrogen Inorganic materials 0.000 claims description 88
- 239000001257 hydrogen Substances 0.000 claims description 76
- 150000002431 hydrogen Chemical class 0.000 claims description 72
- -1 OR 9 Chemical group 0.000 claims description 63
- 125000004429 atom Chemical group 0.000 claims description 48
- 239000012453 solvate Substances 0.000 claims description 47
- 229940002612 prodrug Drugs 0.000 claims description 42
- 239000000651 prodrug Substances 0.000 claims description 42
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 40
- 150000002367 halogens Chemical class 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000003107 substituted aryl group Chemical group 0.000 claims description 25
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 15
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 230000019552 anatomical structure morphogenesis Effects 0.000 claims description 4
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 208000002672 hepatitis B Diseases 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000006384 methylpyridyl group Chemical group 0.000 claims description 4
- BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 230000010076 replication Effects 0.000 claims description 3
- JNHULJPDNUCLHD-UHFFFAOYSA-N 5-[[3-[(4-methoxyphenyl)carbamoyl]phenyl]sulfonylamino]pentanoic acid Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=CC(S(=O)(=O)NCCCCC(O)=O)=C1 JNHULJPDNUCLHD-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 125000004342 dicyclopropylmethyl group Chemical group [H]C1([H])C([H])([H])C1([H])C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 208000019423 liver disease Diseases 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- FVMAYATYZSYSFZ-UHFFFAOYSA-N n-(3-methoxy-5-phenoxypyridin-2-yl)-3-pyrrolidin-1-ylsulfonylbenzamide Chemical compound C=1N=C(NC(=O)C=2C=C(C=CC=2)S(=O)(=O)N2CCCC2)C(OC)=CC=1OC1=CC=CC=C1 FVMAYATYZSYSFZ-UHFFFAOYSA-N 0.000 claims description 2
- WFLQINZNNVGHIX-UHFFFAOYSA-N n-(3-methoxy-5-phenylsulfanylpyridin-2-yl)-3-pyrrolidin-1-ylsulfonylbenzamide Chemical compound C=1N=C(NC(=O)C=2C=C(C=CC=2)S(=O)(=O)N2CCCC2)C(OC)=CC=1SC1=CC=CC=C1 WFLQINZNNVGHIX-UHFFFAOYSA-N 0.000 claims description 2
- NPZTXJPMHHMWHQ-UHFFFAOYSA-N n-(5-bromo-3-methoxypyridin-2-yl)-3-piperidin-1-ylsulfonylbenzamide Chemical compound COC1=CC(Br)=CN=C1NC(=O)C1=CC=CC(S(=O)(=O)N2CCCCC2)=C1 NPZTXJPMHHMWHQ-UHFFFAOYSA-N 0.000 claims description 2
- SEFGEXQGNGLZAG-UHFFFAOYSA-N n-(5-ethenyl-3-methoxypyridin-2-yl)-3-piperidin-1-ylsulfonylbenzamide Chemical compound COC1=CC(C=C)=CN=C1NC(=O)C1=CC=CC(S(=O)(=O)N2CCCCC2)=C1 SEFGEXQGNGLZAG-UHFFFAOYSA-N 0.000 claims description 2
- MAQWAGCJOFDDNU-UHFFFAOYSA-N n-(5-ethyl-3-methoxypyridin-2-yl)-3-piperidin-1-ylsulfonylbenzamide Chemical compound COC1=CC(CC)=CN=C1NC(=O)C1=CC=CC(S(=O)(=O)N2CCCCC2)=C1 MAQWAGCJOFDDNU-UHFFFAOYSA-N 0.000 claims description 2
- 230000007170 pathology Effects 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 150000004885 piperazines Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 45
- 239000002904 solvent Substances 0.000 claims 24
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- 150000004677 hydrates Chemical class 0.000 claims 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 0 CC1=CCCC(C2(*)CC2)=C1 Chemical compound CC1=CCCC(C2(*)CC2)=C1 0.000 description 32
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 238000000034 method Methods 0.000 description 5
- DQOGDQIDOONUSK-REOHCLBHSA-N C[C@H](C(F)(F)F)C(O)=O Chemical compound C[C@H](C(F)(F)F)C(O)=O DQOGDQIDOONUSK-REOHCLBHSA-N 0.000 description 4
- DQOGDQIDOONUSK-UWTATZPHSA-N C[C@@H](C(F)(F)F)C(O)=O Chemical compound C[C@@H](C(F)(F)F)C(O)=O DQOGDQIDOONUSK-UWTATZPHSA-N 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- FILOYPQPSRQLRL-NRFANRHFSA-N 3-piperidin-1-ylsulfonyl-n-[(1s)-1,2,3,4-tetrahydronaphthalen-1-yl]benzamide Chemical compound N([C@@H]1C2=CC=CC=C2CCC1)C(=O)C(C=1)=CC=CC=1S(=O)(=O)N1CCCCC1 FILOYPQPSRQLRL-NRFANRHFSA-N 0.000 description 1
- BGNWXRJWDQHCRB-UHFFFAOYSA-N CC(C)c1ncccn1 Chemical compound CC(C)c1ncccn1 BGNWXRJWDQHCRB-UHFFFAOYSA-N 0.000 description 1
- WPPZHQBTLCZSEY-UHFFFAOYSA-N CC1(C)N=CC=C(C)N1 Chemical compound CC1(C)N=CC=C(C)N1 WPPZHQBTLCZSEY-UHFFFAOYSA-N 0.000 description 1
- ZHUGZTZOGHQIOD-UHFFFAOYSA-N CC1(C)OC(C)=NC=C1 Chemical compound CC1(C)OC(C)=NC=C1 ZHUGZTZOGHQIOD-UHFFFAOYSA-N 0.000 description 1
- LRNKDEJJYFZZOV-SCSAIBSYSA-N C[C@@H](C(F)(F)F)C(OC1(CC1)C(O)=O)=O Chemical compound C[C@@H](C(F)(F)F)C(OC1(CC1)C(O)=O)=O LRNKDEJJYFZZOV-SCSAIBSYSA-N 0.000 description 1
- FZMPLKVGINKUJZ-UHFFFAOYSA-N Cc(cc1F)ccc1F Chemical compound Cc(cc1F)ccc1F FZMPLKVGINKUJZ-UHFFFAOYSA-N 0.000 description 1
- BPWJEVHPHKDCLD-UHFFFAOYSA-N O=C(c(cc1)cc(F)c1F)NC(CC1S(NC2CC2)(=O)=O)=CC=C1F Chemical compound O=C(c(cc1)cc(F)c1F)NC(CC1S(NC2CC2)(=O)=O)=CC=C1F BPWJEVHPHKDCLD-UHFFFAOYSA-N 0.000 description 1
- FABZZCLPYQXJEY-UHFFFAOYSA-N O=C(c(cc1)cc(F)c1F)Nc(cc1NS(C2CC2)(=O)=O)ccc1F Chemical compound O=C(c(cc1)cc(F)c1F)Nc(cc1NS(C2CC2)(=O)=O)ccc1F FABZZCLPYQXJEY-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261746552P | 2012-12-27 | 2012-12-27 | |
| US61/746,552 | 2012-12-27 | ||
| PCT/US2013/077940 WO2014106019A2 (en) | 2012-12-27 | 2013-12-27 | Novel antiviral agents against hbv infection |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018177094A Division JP2019034943A (ja) | 2012-12-27 | 2018-09-21 | Ｈｂｖ感染に対する新規抗ウイルス剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016509591A JP2016509591A (ja) | 2016-03-31 |
| JP2016509591A5 true JP2016509591A5 (enExample) | 2016-07-21 |
| JP6409001B2 JP6409001B2 (ja) | 2018-10-17 |
Family
ID=51022201
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015550788A Expired - Fee Related JP6409001B2 (ja) | 2012-12-27 | 2013-12-27 | Ｈｂｖ感染に対する新規抗ウイルス剤 |
| JP2018177094A Pending JP2019034943A (ja) | 2012-12-27 | 2018-09-21 | Ｈｂｖ感染に対する新規抗ウイルス剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018177094A Pending JP2019034943A (ja) | 2012-12-27 | 2018-09-21 | Ｈｂｖ感染に対する新規抗ウイルス剤 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US9938236B2 (enExample) |
| EP (1) | EP2938338A4 (enExample) |
| JP (2) | JP6409001B2 (enExample) |
| KR (1) | KR101942151B1 (enExample) |
| CN (1) | CN105209031A (enExample) |
| AU (2) | AU2013370300B2 (enExample) |
| BR (1) | BR112015015584A2 (enExample) |
| CA (1) | CA2896554C (enExample) |
| EA (1) | EA201591220A1 (enExample) |
| HK (1) | HK1217649A1 (enExample) |
| IL (2) | IL239397B (enExample) |
| MX (1) | MX2015008471A (enExample) |
| PH (1) | PH12015501473A1 (enExample) |
| SG (2) | SG11201504740UA (enExample) |
| WO (1) | WO2014106019A2 (enExample) |
Families Citing this family (116)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5977837B2 (ja) | 2011-12-21 | 2016-08-24 | ノヴィラ・セラピューティクス・インコーポレイテッド | Ｂ型肝炎抗ウイルス剤 |
| MX373711B (es) | 2012-08-28 | 2020-05-08 | Janssen Sciences Ireland Uc | Sulfamoilarilamidas y su uso como medicamentos para el tratamiento de la hepatitis b. |
| EP2938338A4 (en) * | 2012-12-27 | 2016-11-23 | Univ Drexel | NOVEL ANTIVIRAL AGENTS AGAINST HBV INFECTION |
| DK2961732T3 (en) | 2013-02-28 | 2017-07-10 | Janssen Sciences Ireland Uc | SULFAMOYLARYLAMIDS AND USE THEREOF AS MEDICINES TO TREAT HEPATITIS B |
| CN105102451B (zh) | 2013-04-03 | 2018-09-18 | 爱尔兰詹森科学公司 | N-苯基-氨甲酰衍生物及其作为药物用于治疗乙型肝炎的用途 |
| JO3603B1 (ar) | 2013-05-17 | 2020-07-05 | Janssen Sciences Ireland Uc | مشتقات سلفامويل بيرولاميد واستخدامها كادوية لمعالجة التهاب الكبد نوع بي |
| KR102244937B1 (ko) | 2013-07-25 | 2021-04-27 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 글리옥사미드 치환된 피롤아미드 유도체 및 ｂ형 간염 치료용 의약으로서의 이의 용도 |
| DK3060547T3 (en) | 2013-10-23 | 2018-01-15 | Janssen Sciences Ireland Uc | CARBOXAMIDE DERIVATIVES AND USE THEREOF AS MEDICINES FOR TREATMENT OF HEPATITS B |
| US9169212B2 (en) | 2014-01-16 | 2015-10-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
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| US11078193B2 (en) | 2014-02-06 | 2021-08-03 | Janssen Sciences Ireland Uc | Sulphamoylpyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
| CN110437153A (zh) | 2014-03-13 | 2019-11-12 | 美国印第安纳大学研究和技术公司 | 乙型肝炎核心蛋白变构调节剂 |
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| WO2015172128A1 (en) * | 2014-05-09 | 2015-11-12 | Indiana University Research And Technology Corporation | Methods and compositions for treating hepatitis b virus infections |
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2013
- 2013-12-27 EP EP13868405.5A patent/EP2938338A4/en not_active Withdrawn
- 2013-12-27 CN CN201380072796.5A patent/CN105209031A/zh active Pending
- 2013-12-27 SG SG11201504740UA patent/SG11201504740UA/en unknown
- 2013-12-27 SG SG10201803698UA patent/SG10201803698UA/en unknown
- 2013-12-27 JP JP2015550788A patent/JP6409001B2/ja not_active Expired - Fee Related
- 2013-12-27 AU AU2013370300A patent/AU2013370300B2/en not_active Ceased
- 2013-12-27 CA CA2896554A patent/CA2896554C/en not_active Expired - Fee Related
- 2013-12-27 BR BR112015015584A patent/BR112015015584A2/pt not_active Application Discontinuation
- 2013-12-27 HK HK16105705.7A patent/HK1217649A1/zh unknown
- 2013-12-27 US US14/759,385 patent/US9938236B2/en not_active Expired - Fee Related
- 2013-12-27 MX MX2015008471A patent/MX2015008471A/es unknown
- 2013-12-27 KR KR1020157020432A patent/KR101942151B1/ko not_active Expired - Fee Related
- 2013-12-27 EA EA201591220A patent/EA201591220A1/ru unknown
- 2013-12-27 WO PCT/US2013/077940 patent/WO2014106019A2/en not_active Ceased
-
2015
- 2015-06-14 IL IL239397A patent/IL239397B/en not_active IP Right Cessation
- 2015-06-26 PH PH12015501473A patent/PH12015501473A1/en unknown
-
2018
- 2018-03-11 IL IL258007A patent/IL258007A/en unknown
- 2018-03-22 US US15/933,098 patent/US20180230092A1/en not_active Abandoned
- 2018-09-21 JP JP2018177094A patent/JP2019034943A/ja active Pending
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2019
- 2019-01-31 AU AU2019200663A patent/AU2019200663A1/en not_active Abandoned
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