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
- Authority
- 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.)
- Granted
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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 (esLanguage) | 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 (esLanguage) |
| EP (1) | EP2938338A4 (esLanguage) |
| JP (2) | JP6409001B2 (esLanguage) |
| KR (1) | KR101942151B1 (esLanguage) |
| CN (1) | CN105209031A (esLanguage) |
| AU (2) | AU2013370300B2 (esLanguage) |
| BR (1) | BR112015015584A2 (esLanguage) |
| CA (1) | CA2896554C (esLanguage) |
| EA (1) | EA201591220A1 (esLanguage) |
| HK (1) | HK1217649A1 (esLanguage) |
| IL (2) | IL239397B (esLanguage) |
| MX (1) | MX2015008471A (esLanguage) |
| PH (1) | PH12015501473A1 (esLanguage) |
| SG (2) | SG11201504740UA (esLanguage) |
| WO (1) | WO2014106019A2 (esLanguage) |
Families Citing this family (116)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2797123T3 (es) | 2011-12-21 | 2020-12-01 | Novira Therapeutics Inc | Agentes antivirales para la hepatitis B |
| CN104902885A (zh) | 2012-08-28 | 2015-09-09 | 爱尔兰詹森科学公司 | 氨磺酰基-芳基酰胺和其作为药物用于治疗乙型肝炎的用途 |
| JP6409001B2 (ja) * | 2012-12-27 | 2018-10-17 | ドレクセル ユニバーシティ | Ｈｂｖ感染に対する新規抗ウイルス剤 |
| PL2961732T3 (pl) | 2013-02-28 | 2017-09-29 | Janssen Sciences Ireland Uc | Sulfamoilo-aryloamidy i ich stosowanie jako leków do leczenia wirusowego zapalenia wątroby typu B |
| EA027068B1 (ru) | 2013-04-03 | 2017-06-30 | Янссен Сайенсиз Айрлэнд Юси | Производные n-фенилкарбоксамида и их применение в качестве лекарственных препаратов для лечения гепатита b |
| JO3603B1 (ar) | 2013-05-17 | 2020-07-05 | Janssen Sciences Ireland Uc | مشتقات سلفامويل بيرولاميد واستخدامها كادوية لمعالجة التهاب الكبد نوع بي |
| EP3357906B1 (en) | 2013-07-25 | 2019-12-04 | Janssen Sciences Ireland Unlimited Company | Glyoxamide substituted pyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
| JP6452119B2 (ja) | 2013-10-23 | 2019-01-16 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | カルボキサミド誘導体およびｂ型肝炎の処置のための医薬品としてのその使用 |
| 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 |
| US20150216938A1 (en) * | 2014-02-05 | 2015-08-06 | Novira Therapeutics Inc. | Combination therapy for treatment of hbv infections |
| HK1225389A1 (zh) | 2014-02-06 | 2017-09-08 | Janssen Sciences Ireland Uc | 氨磺酰基吡咯酰胺衍生物及其作为药物用於治疗乙型肝炎的用途 |
| KR102363174B1 (ko) | 2014-03-13 | 2022-02-15 | 인디애나 유니버시티 리서치 앤드 테크놀로지 코포레이션 | B형 간염 코어 단백질 알로스테릭 조정제 |
| US9400280B2 (en) | 2014-03-27 | 2016-07-26 | Novira Therapeutics, Inc. | Piperidine derivatives and methods of treating hepatitis B infections |
| EP3139954A4 (en) * | 2014-05-09 | 2018-02-28 | Indiana University Research and Technology Corporation | Methods and compositions for treating hepatitis b virus infections |
| ES2802412T3 (es) * | 2014-12-02 | 2021-01-19 | Novira Therapeutics Inc | Compuestos de sulfonamida inversa a base de sulfuro, alquilo y piridilo para el tratamiento del VHB |
| US9597332B2 (en) | 2014-12-02 | 2017-03-21 | Novira Therapeutics, Inc. | Sulfide alkyl compounds for HBV treatment |
| MA41140A (fr) | 2014-12-12 | 2017-10-17 | Cancer Research Tech Ltd | Dérivés de 2,4-dioxo-quinazoline-6-sulfonamide en tant qu'inhibiteurs de la parg |
| MA41179A (fr) | 2014-12-19 | 2017-10-24 | Cancer Research Tech Ltd | Composés inhibiteurs de parg |
| EP3240537B1 (en) | 2014-12-30 | 2020-09-09 | F. Hoffmann-La Roche AG | Novel tetrahydropyridopyrimidines and tetrahydropyridopyridines for the treatment and prophylaxis of hepatitis b virus infection |
| US9765050B2 (en) | 2014-12-30 | 2017-09-19 | Novira Therapeutics, Inc. | Pyridyl reverse sulfonamides for HBV treatment |
| CA2980298A1 (en) | 2015-03-19 | 2016-09-22 | Novira Therapeutics, Inc. | Azocane and azonane derivatives and methods of treating hepatitis b infections |
| US10442788B2 (en) | 2015-04-01 | 2019-10-15 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| JP6462155B2 (ja) * | 2015-05-04 | 2019-01-30 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | Ｂ型肝炎ウイルス感染症の治療用のＨＢｓＡｇ（ＨＢＶ表面抗原）及びＨＢＶ ＤＮＡ産生の阻害剤としてのテトラヒドロピリドピリミジン類及びテトラヒドロピリドピリジン類 |
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| US10875876B2 (en) | 2015-07-02 | 2020-12-29 | Janssen Sciences Ireland Uc | Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
| US10179131B2 (en) | 2015-07-13 | 2019-01-15 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| TWI786639B (zh) | 2015-09-15 | 2022-12-11 | 美商艾森伯利生物科學公司 | B型肝炎核心蛋白質調節劑 |
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