AU2014222641B2 - Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of Hepatitis B - Google Patents
Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of Hepatitis B Download PDFInfo
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- AU2014222641B2 AU2014222641B2 AU2014222641A AU2014222641A AU2014222641B2 AU 2014222641 B2 AU2014222641 B2 AU 2014222641B2 AU 2014222641 A AU2014222641 A AU 2014222641A AU 2014222641 A AU2014222641 A AU 2014222641A AU 2014222641 B2 AU2014222641 B2 AU 2014222641B2
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- compound
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- hbv
- methyl
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- 238000011282 treatment Methods 0.000 title claims description 16
- 239000003814 drug Substances 0.000 title claims description 11
- 208000002672 hepatitis B Diseases 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 238000000034 method Methods 0.000 claims abstract description 102
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000003112 inhibitor Substances 0.000 claims abstract description 11
- 239000012453 solvate Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 208000015181 infectious disease Diseases 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 230000010076 replication Effects 0.000 abstract description 4
- 150000004677 hydrates Chemical class 0.000 abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 241000700721 Hepatitis B virus Species 0.000 description 48
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 150000001412 amines Chemical class 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- 238000010626 work up procedure Methods 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- -1 Sulphamoyl Chemical group 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
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- 239000011541 reaction mixture Substances 0.000 description 14
- NQTBKYKRAOANGR-UHFFFAOYSA-N 3-[(4-fluoro-3-methylphenyl)carbamoyl]benzenesulfonyl chloride Chemical compound C1=C(F)C(C)=CC(NC(=O)C=2C=C(C=CC=2)S(Cl)(=O)=O)=C1 NQTBKYKRAOANGR-UHFFFAOYSA-N 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 11
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000003480 eluent Substances 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
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- 239000010410 layer Substances 0.000 description 8
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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- 230000000840 anti-viral effect Effects 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
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- 239000000047 product Substances 0.000 description 6
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- 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 5
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
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- 238000010828 elution Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 102000053602 DNA Human genes 0.000 description 4
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- 239000007821 HATU Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 4
- JJOITZMHKRXAAL-UHFFFAOYSA-N n-(4-fluoro-3-methylphenyl)-3-(2-methylaziridin-1-yl)sulfonylbenzamide Chemical compound CC1CN1S(=O)(=O)C1=CC=CC(C(=O)NC=2C=C(C)C(F)=CC=2)=C1 JJOITZMHKRXAAL-UHFFFAOYSA-N 0.000 description 4
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- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 3
- DLKOQYCBVTYRJA-UHFFFAOYSA-N 3-(1-aminopropan-2-ylsulfamoyl)-n-(4-fluoro-3-methylphenyl)benzamide Chemical compound NCC(C)NS(=O)(=O)C1=CC=CC(C(=O)NC=2C=C(C)C(F)=CC=2)=C1 DLKOQYCBVTYRJA-UHFFFAOYSA-N 0.000 description 3
- NYMDPDNETOLVBS-UHFFFAOYSA-N 4-fluoro-3-methylaniline Chemical compound CC1=CC(N)=CC=C1F NYMDPDNETOLVBS-UHFFFAOYSA-N 0.000 description 3
- LIANSSSABWUTRH-UHFFFAOYSA-N 5-chlorosulfonyl-2-methylbenzoyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1C(Cl)=O LIANSSSABWUTRH-UHFFFAOYSA-N 0.000 description 3
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- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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- Molecular Biology (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (5)
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| EP13157232 | 2013-02-28 | ||
| EP13157232.3 | 2013-02-28 | ||
| EP13170069.2 | 2013-05-31 | ||
| EP13170069 | 2013-05-31 | ||
| PCT/EP2014/053858 WO2014131847A1 (en) | 2013-02-28 | 2014-02-27 | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b |
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| AU2014222641A1 AU2014222641A1 (en) | 2015-08-13 |
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| JP (1) | JP6466348B2 (enExample) |
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| EA026368B1 (ru) | 2011-12-21 | 2017-03-31 | Новира Терапьютикс, Инк. | Противовирусные агенты против гепатита в |
| AU2013307337B2 (en) * | 2012-08-28 | 2018-07-19 | Janssen Sciences Ireland Uc | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of Hepatitis B |
| CN105189453B (zh) | 2013-02-28 | 2018-04-10 | 爱尔兰詹森科学公司 | 氨磺酰基‑芳基酰胺及其作为用于乙型肝炎治疗的药物的用途 |
| WO2014165128A2 (en) | 2013-03-12 | 2014-10-09 | Novira Therapeutics, Inc. | Hepatitis b antiviral agents |
| WO2014161888A1 (en) | 2013-04-03 | 2014-10-09 | Janssen R&D Ireland | N-phenyl-carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
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2014
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| DK2961732T3 (en) | 2017-07-10 |
| JP2016515096A (ja) | 2016-05-26 |
| CA2899706C (en) | 2021-10-19 |
| CN105189453B (zh) | 2018-04-10 |
| HUE034820T2 (en) | 2018-02-28 |
| HRP20170945T1 (hr) | 2017-09-22 |
| SI2961732T1 (sl) | 2017-07-31 |
| CA2899706A1 (en) | 2014-09-04 |
| IL240213A0 (en) | 2015-09-24 |
| ES2628953T3 (es) | 2017-08-04 |
| EP2961732B1 (en) | 2017-04-12 |
| MX2015011229A (es) | 2016-02-03 |
| US10125094B2 (en) | 2018-11-13 |
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| AU2014222641A1 (en) | 2015-08-13 |
| EP2961732A1 (en) | 2016-01-06 |
| PL2961732T3 (pl) | 2017-09-29 |
| JP6466348B2 (ja) | 2019-02-06 |
| US20190077749A1 (en) | 2019-03-14 |
| WO2014131847A1 (en) | 2014-09-04 |
| US10941113B2 (en) | 2021-03-09 |
| IL240213A (en) | 2016-10-31 |
| EA201591586A1 (ru) | 2015-12-30 |
| MX366123B (es) | 2019-06-27 |
| EA027194B1 (ru) | 2017-06-30 |
| US20160002155A1 (en) | 2016-01-07 |
| CN105189453A (zh) | 2015-12-23 |
| BR112015020242A2 (pt) | 2017-07-18 |
| HK1218110A1 (zh) | 2017-02-03 |
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