CA2980298A1 - Azocane and azonane derivatives and methods of treating hepatitis b infections - Google Patents
Azocane and azonane derivatives and methods of treating hepatitis b infections Download PDFInfo
- Publication number
- CA2980298A1 CA2980298A1 CA2980298A CA2980298A CA2980298A1 CA 2980298 A1 CA2980298 A1 CA 2980298A1 CA 2980298 A CA2980298 A CA 2980298A CA 2980298 A CA2980298 A CA 2980298A CA 2980298 A1 CA2980298 A1 CA 2980298A1
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- Prior art keywords
- compound
- alkyl
- halo
- individual
- hbv
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 102
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 title description 2
- NRHDCQLCSOWVTF-UHFFFAOYSA-N azonane Chemical class C1CCCCNCCC1 NRHDCQLCSOWVTF-UHFFFAOYSA-N 0.000 title description 2
- 208000002672 hepatitis B Diseases 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 354
- 208000015181 infectious disease Diseases 0.000 claims abstract description 69
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 192
- 241000700721 Hepatitis B virus Species 0.000 claims description 139
- 210000000234 capsid Anatomy 0.000 claims description 61
- 150000003839 salts Chemical class 0.000 claims description 57
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 49
- 102000014150 Interferons Human genes 0.000 claims description 42
- 108010050904 Interferons Proteins 0.000 claims description 42
- 239000003814 drug Substances 0.000 claims description 37
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 34
- 230000003612 virological effect Effects 0.000 claims description 33
- 229940079322 interferon Drugs 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- -1 -H2PO4 Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 229940124597 therapeutic agent Drugs 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 230000000840 anti-viral effect Effects 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 19
- 239000003112 inhibitor Substances 0.000 claims description 18
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- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims description 10
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 10
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- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims description 5
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 claims description 5
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- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 5
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 claims description 5
- HDOVUKNUBWVHOX-QMMMGPOBSA-N Valacyclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 HDOVUKNUBWVHOX-QMMMGPOBSA-N 0.000 claims description 5
- WPVFJKSGQUFQAP-GKAPJAKFSA-N Valcyte Chemical compound N1C(N)=NC(=O)C2=C1N(COC(CO)COC(=O)[C@@H](N)C(C)C)C=N2 WPVFJKSGQUFQAP-GKAPJAKFSA-N 0.000 claims description 5
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- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 5
- RYMCFYKJDVMSIR-RNFRBKRXSA-N apricitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1S[C@H](CO)OC1 RYMCFYKJDVMSIR-RNFRBKRXSA-N 0.000 claims description 5
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- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 claims description 5
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- 229960004396 famciclovir Drugs 0.000 claims description 5
- GGXKWVWZWMLJEH-UHFFFAOYSA-N famcyclovir Chemical compound N1=C(N)N=C2N(CCC(COC(=O)C)COC(C)=O)C=NC2=C1 GGXKWVWZWMLJEH-UHFFFAOYSA-N 0.000 claims description 5
- 229960002963 ganciclovir Drugs 0.000 claims description 5
- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 claims description 5
- 229960003130 interferon gamma Drugs 0.000 claims description 5
- 229960000689 nevirapine Drugs 0.000 claims description 5
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- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 5
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- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 5
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- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 claims description 5
- WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 claims description 4
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- FEFIBEHSXLKJGI-UHFFFAOYSA-N methyl 2-[3-[[3-(6-amino-2-butoxy-8-oxo-7h-purin-9-yl)propyl-(3-morpholin-4-ylpropyl)amino]methyl]phenyl]acetate Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)N1CCCN(CC=1C=C(CC(=O)OC)C=CC=1)CCCN1CCOCC1 FEFIBEHSXLKJGI-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001475 halogen functional group Chemical group 0.000 claims 33
- YYCDGEZXHXHLGW-UHFFFAOYSA-N 6-amino-9-benzyl-2-(2-methoxyethoxy)-7h-purin-8-one Chemical compound C12=NC(OCCOC)=NC(N)=C2NC(=O)N1CC1=CC=CC=C1 YYCDGEZXHXHLGW-UHFFFAOYSA-N 0.000 claims 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
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- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/5545—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having eight-membered rings not containing additional condensed or non-condensed nitrogen-containing 3-7 membered rings
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- A—HUMAN NECESSITIES
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- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/21—Interferons [IFN]
- A61K38/212—IFN-alpha
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/02—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/22—Eight-membered rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
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- Oncology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562135243P | 2015-03-19 | 2015-03-19 | |
| US62/135,243 | 2015-03-19 | ||
| PCT/US2016/023066 WO2016149581A1 (en) | 2015-03-19 | 2016-03-18 | Azocane and azonane derivatives and methods of treating hepatitis b infections |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2980298A1 true CA2980298A1 (en) | 2016-09-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2980298A Abandoned CA2980298A1 (en) | 2015-03-19 | 2016-03-18 | Azocane and azonane derivatives and methods of treating hepatitis b infections |
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| Country | Link |
|---|---|
| US (2) | US9884831B2 (OSRAM) |
| EP (1) | EP3271019A1 (OSRAM) |
| JP (1) | JP2018510159A (OSRAM) |
| CN (1) | CN107847762A (OSRAM) |
| AU (1) | AU2016232801A1 (OSRAM) |
| CA (1) | CA2980298A1 (OSRAM) |
| EA (1) | EA201792069A1 (OSRAM) |
| HK (1) | HK1247147A1 (OSRAM) |
| WO (1) | WO2016149581A1 (OSRAM) |
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| SG11201402660YA (en) | 2011-12-21 | 2014-10-30 | Novira Therapeutics Inc | Hepatitis b antiviral agents |
| SG10201605291WA (en) | 2012-08-28 | 2016-08-30 | Janssen Sciences Ireland Uc | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b |
| PT2961732T (pt) | 2013-02-28 | 2017-06-26 | Janssen Sciences Ireland Uc | Sulfamoil-arilamidas e utilização das mesmas como medicamentos para o tratamento de hepatite b |
| MX353412B (es) | 2013-04-03 | 2018-01-10 | Janssen Sciences Ireland Uc | Derivados de n-fenil-carboxamida y su uso como medicamentos para el tratamiento de la hepatitis b. |
| CA2909742C (en) | 2013-05-17 | 2020-08-04 | Janssen Sciences Ireland Uc | Sulphamoylthiophenamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
| JO3603B1 (ar) | 2013-05-17 | 2020-07-05 | Janssen Sciences Ireland Uc | مشتقات سلفامويل بيرولاميد واستخدامها كادوية لمعالجة التهاب الكبد نوع بي |
| LT3024819T (lt) | 2013-07-25 | 2018-06-11 | Janssen Sciences Ireland Uc | Pirolamido dariniai, turintys glioksamido pakaitų, ir jų panaudojimas kaip vaistų hepatito b gydymui |
| NZ717629A (en) | 2013-10-23 | 2021-12-24 | Janssen Sciences Ireland Uc | Carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis 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 |
| US20150216938A1 (en) | 2014-02-05 | 2015-08-06 | Novira Therapeutics Inc. | Combination therapy for treatment of hbv infections |
| DK3102572T3 (en) | 2014-02-06 | 2019-02-04 | Janssen Sciences Ireland Uc | SULFAMOYLPYRROLAMIDE DERIVATIVES AND THEIR USE AS MEDICINES TO TREAT HEPATITIS B |
| HK1247147A1 (zh) | 2015-03-19 | 2018-09-21 | 诺维拉治疗公司 | 氮杂环辛烷和氮杂环壬烷衍生物以及治疗乙型肝炎感染的方法 |
| 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 |
| AR106192A1 (es) | 2015-09-29 | 2017-12-20 | Novira Therapeutics Inc | Formas cristalinas de un agente antiviral contra la hepatitis b |
| WO2017181141A2 (en) | 2016-04-15 | 2017-10-19 | Novira Therapeutics, Inc. | Combinations and methods comprising a capsid assembly inhibitor |
| WO2019175657A1 (en) | 2018-03-14 | 2019-09-19 | Janssen Sciences Ireland Unlimited Company | Capsid assembly modulator dosing regimen |
| BR112021007602A2 (pt) * | 2018-10-22 | 2021-07-27 | Assembly Biosciences, Inc. | compostos de heteroaril carboxamida de 5 membros para tratamento de hbv |
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-
2016
- 2016-03-18 HK HK18106759.8A patent/HK1247147A1/zh unknown
- 2016-03-18 CA CA2980298A patent/CA2980298A1/en not_active Abandoned
- 2016-03-18 WO PCT/US2016/023066 patent/WO2016149581A1/en not_active Ceased
- 2016-03-18 CN CN201680028649.1A patent/CN107847762A/zh active Pending
- 2016-03-18 EP EP16712665.5A patent/EP3271019A1/en not_active Withdrawn
- 2016-03-18 AU AU2016232801A patent/AU2016232801A1/en not_active Abandoned
- 2016-03-18 US US15/073,965 patent/US9884831B2/en not_active Expired - Fee Related
- 2016-03-18 JP JP2017549199A patent/JP2018510159A/ja active Pending
- 2016-03-18 EA EA201792069A patent/EA201792069A1/ru unknown
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2017
- 2017-12-20 US US15/848,639 patent/US10537580B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016149581A1 (en) | 2016-09-22 |
| EA201792069A1 (ru) | 2018-04-30 |
| EP3271019A1 (en) | 2018-01-24 |
| US20180201590A1 (en) | 2018-07-19 |
| US10537580B2 (en) | 2020-01-21 |
| US20160272599A1 (en) | 2016-09-22 |
| AU2016232801A1 (en) | 2017-10-12 |
| JP2018510159A (ja) | 2018-04-12 |
| US9884831B2 (en) | 2018-02-06 |
| CN107847762A (zh) | 2018-03-27 |
| HK1247147A1 (zh) | 2018-09-21 |
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