JP6441315B2 - スルファモイルチオフェンアミド誘導体およびｂ型肝炎を治療するための医薬品としてのその使用 - Google Patents
スルファモイルチオフェンアミド誘導体およびｂ型肝炎を治療するための医薬品としてのその使用 Download PDFInfo
- Publication number
- JP6441315B2 JP6441315B2 JP2016513394A JP2016513394A JP6441315B2 JP 6441315 B2 JP6441315 B2 JP 6441315B2 JP 2016513394 A JP2016513394 A JP 2016513394A JP 2016513394 A JP2016513394 A JP 2016513394A JP 6441315 B2 JP6441315 B2 JP 6441315B2
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- Prior art keywords
- compound
- methyl
- mmol
- pharmaceutically acceptable
- thiophene
- 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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- 239000003814 drug Substances 0.000 title claims description 9
- 208000002672 hepatitis B Diseases 0.000 title description 2
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- 150000001875 compounds Chemical class 0.000 claims description 126
- -1 C 1 -C 3 alkyl Chemical group 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 59
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
- 229910052731 fluorine Inorganic materials 0.000 claims description 50
- 125000001153 fluoro group Chemical group F* 0.000 claims description 37
- 229920006395 saturated elastomer Polymers 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000012453 solvate Substances 0.000 claims description 21
- 208000015181 infectious disease Diseases 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 claims description 11
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- 125000001424 substituent group Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 48
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- 229940125878 compound 36 Drugs 0.000 description 10
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- PVAJJAQXMPHKEV-UHFFFAOYSA-N 5-chlorosulfonyl-2-methylthiophene-3-carbonyl chloride Chemical compound Cc1sc(cc1C(Cl)=O)S(Cl)(=O)=O PVAJJAQXMPHKEV-UHFFFAOYSA-N 0.000 description 8
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- 230000000694 effects Effects 0.000 description 7
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 7
- ISYXXORXVFRVKD-UHFFFAOYSA-N 3,4-difluoro-5-methylaniline Chemical compound CC1=CC(N)=CC(F)=C1F ISYXXORXVFRVKD-UHFFFAOYSA-N 0.000 description 6
- IKWDNQBCRWYWEP-UHFFFAOYSA-N 4-[(3,4-difluorophenyl)carbamoyl]-5-methylthiophene-2-sulfonyl chloride Chemical compound Cc1sc(cc1C(=O)Nc1ccc(F)c(F)c1)S(Cl)(=O)=O IKWDNQBCRWYWEP-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
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- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
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- JLPJFSCQKHRSQR-UHFFFAOYSA-N oxolan-3-one Chemical compound O=C1CCOC1 JLPJFSCQKHRSQR-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
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- 229920005989 resin Polymers 0.000 description 1
- 238000010839 reverse transcription Methods 0.000 description 1
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- IQFYYKKMVGJFEH-CSMHCCOUSA-N telbivudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 IQFYYKKMVGJFEH-CSMHCCOUSA-N 0.000 description 1
- 229960005311 telbivudine Drugs 0.000 description 1
- 229960004556 tenofovir Drugs 0.000 description 1
- VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 description 1
- XTWWZOLSIVFHCG-UHFFFAOYSA-N tert-butyl N-(3,4-difluoro-5-methylphenyl)carbamate Chemical compound Cc1cc(NC(=O)OC(C)(C)C)cc(F)c1F XTWWZOLSIVFHCG-UHFFFAOYSA-N 0.000 description 1
- NXVYWMRPRBEXRM-UHFFFAOYSA-N tert-butyl n-(3-chloro-4,5-difluorophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC(F)=C(F)C(Cl)=C1 NXVYWMRPRBEXRM-UHFFFAOYSA-N 0.000 description 1
- PWQIGBOSLQHOBT-SSDOTTSWSA-N tert-butyl n-[(2r)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate Chemical compound CON(C)C(=O)[C@@H](C)NC(=O)OC(C)(C)C PWQIGBOSLQHOBT-SSDOTTSWSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
-
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13168295 | 2013-05-17 | ||
| EP13168295.7 | 2013-05-17 | ||
| EP13185227 | 2013-09-19 | ||
| EP13185227.9 | 2013-09-19 | ||
| EP14157917.7 | 2014-03-05 | ||
| EP14157917 | 2014-03-05 | ||
| PCT/EP2014/060132 WO2014184365A1 (en) | 2013-05-17 | 2014-05-16 | Sulphamoylthiophenamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016518437A JP2016518437A (ja) | 2016-06-23 |
| JP2016518437A5 JP2016518437A5 (OSRAM) | 2017-10-12 |
| JP6441315B2 true JP6441315B2 (ja) | 2018-12-19 |
Family
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| JP2016513394A Expired - Fee Related JP6441315B2 (ja) | 2013-05-17 | 2014-05-16 | スルファモイルチオフェンアミド誘導体およびｂ型肝炎を治療するための医薬品としてのその使用 |
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| US (1) | US10160743B2 (OSRAM) |
| EP (1) | EP2997019B1 (OSRAM) |
| JP (1) | JP6441315B2 (OSRAM) |
| CN (1) | CN105960400B (OSRAM) |
| AU (1) | AU2014267235B2 (OSRAM) |
| BR (1) | BR112015028538A2 (OSRAM) |
| CA (1) | CA2909742C (OSRAM) |
| CY (1) | CY1122337T1 (OSRAM) |
| DK (1) | DK2997019T3 (OSRAM) |
| EA (1) | EA035500B1 (OSRAM) |
| ES (1) | ES2695182T3 (OSRAM) |
| HR (1) | HRP20181863T1 (OSRAM) |
| HU (1) | HUE040446T2 (OSRAM) |
| IL (1) | IL242141B (OSRAM) |
| LT (1) | LT2997019T (OSRAM) |
| MX (1) | MX366787B (OSRAM) |
| PL (1) | PL2997019T3 (OSRAM) |
| PT (1) | PT2997019T (OSRAM) |
| RS (1) | RS57999B1 (OSRAM) |
| SI (1) | SI2997019T1 (OSRAM) |
| SM (1) | SMT201800577T1 (OSRAM) |
| WO (1) | WO2014184365A1 (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 |
| US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| US9169212B2 (en) | 2014-01-16 | 2015-10-27 | 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 |
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| HRP20191444T1 (hr) | 2014-03-13 | 2019-11-29 | Univ Indiana Res & Tech Corp | Alosterni modulatori proteina jezgre hepatitisa 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 |
| WO2016161268A1 (en) | 2015-04-01 | 2016-10-06 | Enanta Pharmaceuticals, Inc. | Hepatitis b antviral agents |
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| WO2017011552A1 (en) | 2015-07-13 | 2017-01-19 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
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| WO2017136403A1 (en) | 2016-02-02 | 2017-08-10 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
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| CA2909742A1 (en) | 2014-11-20 |
| CN105960400B (zh) | 2019-05-31 |
| SI2997019T1 (sl) | 2018-12-31 |
| US20160115149A1 (en) | 2016-04-28 |
| DK2997019T3 (en) | 2018-12-03 |
| JP2016518437A (ja) | 2016-06-23 |
| AU2014267235B2 (en) | 2017-10-05 |
| SMT201800577T1 (it) | 2019-01-11 |
| CA2909742C (en) | 2020-08-04 |
| RS57999B1 (sr) | 2019-01-31 |
| CN105960400A (zh) | 2016-09-21 |
| AU2014267235A8 (en) | 2015-12-10 |
| CY1122337T1 (el) | 2020-07-31 |
| PL2997019T3 (pl) | 2019-03-29 |
| HUE040446T2 (hu) | 2019-03-28 |
| EA035500B1 (ru) | 2020-06-25 |
| PT2997019T (pt) | 2018-11-21 |
| WO2014184365A1 (en) | 2014-11-20 |
| EP2997019A1 (en) | 2016-03-23 |
| ES2695182T3 (es) | 2019-01-02 |
| AU2014267235A1 (en) | 2015-11-12 |
| HK1225387A1 (zh) | 2017-09-08 |
| IL242141B (en) | 2019-09-26 |
| US10160743B2 (en) | 2018-12-25 |
| MX366787B (es) | 2019-07-23 |
| LT2997019T (lt) | 2018-11-26 |
| EP2997019B1 (en) | 2018-08-08 |
| EA201592198A1 (ru) | 2016-03-31 |
| BR112015028538A2 (pt) | 2017-07-25 |
| MX2015015771A (es) | 2016-03-15 |
| HRP20181863T1 (hr) | 2018-12-28 |
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