AU2022421952A1 - Arylsulphonamide compounds - Google Patents
Arylsulphonamide compounds Download PDFInfo
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- AU2022421952A1 AU2022421952A1 AU2022421952A AU2022421952A AU2022421952A1 AU 2022421952 A1 AU2022421952 A1 AU 2022421952A1 AU 2022421952 A AU2022421952 A AU 2022421952A AU 2022421952 A AU2022421952 A AU 2022421952A AU 2022421952 A1 AU2022421952 A1 AU 2022421952A1
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- Prior art keywords
- optionally substituted
- alkyl
- mmol
- compound
- cycloalkyl
- 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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- 125000004421 aryl sulphonamide group Chemical group 0.000 title description 3
- -1 tautomers Chemical class 0.000 claims abstract description 437
- 150000001875 compounds Chemical class 0.000 claims abstract description 279
- 150000003839 salts Chemical class 0.000 claims abstract description 65
- 239000000651 prodrug Substances 0.000 claims abstract description 55
- 229940002612 prodrug Drugs 0.000 claims abstract description 55
- 239000012453 solvate Substances 0.000 claims abstract description 50
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- 150000001204 N-oxides Chemical class 0.000 claims abstract description 42
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- 238000000034 method Methods 0.000 claims description 231
- 125000000623 heterocyclic group Chemical group 0.000 claims description 116
- 125000003118 aryl group Chemical group 0.000 claims description 94
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 67
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 42
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- 125000003107 substituted aryl group Chemical group 0.000 claims description 33
- 201000010099 disease Diseases 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 17
- 230000002401 inhibitory effect Effects 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
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- 238000011282 treatment Methods 0.000 claims description 7
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- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
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- 125000001475 halogen functional group Chemical group 0.000 claims 8
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 145
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 128
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 123
- 239000007832 Na2SO4 Substances 0.000 description 102
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 102
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 87
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- 239000000543 intermediate Substances 0.000 description 68
- 238000006243 chemical reaction Methods 0.000 description 62
- 239000012267 brine Substances 0.000 description 58
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 58
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 57
- 239000003921 oil Substances 0.000 description 55
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 52
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 46
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 44
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 42
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 40
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- 125000005842 heteroatom Chemical group 0.000 description 36
- 125000005843 halogen group Chemical group 0.000 description 35
- 229910000029 sodium carbonate Inorganic materials 0.000 description 35
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 33
- 238000004809 thin layer chromatography Methods 0.000 description 31
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 30
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- 125000001072 heteroaryl group Chemical group 0.000 description 22
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Classifications
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4355—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
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- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2021904206A AU2021904206A0 (en) | 2021-12-22 | Arylsulphonamide compounds | |
| AU2021904206 | 2021-12-22 | ||
| PCT/AU2022/051568 WO2023115142A1 (en) | 2021-12-22 | 2022-12-22 | Arylsulphonamide compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2022421952A1 true AU2022421952A1 (en) | 2024-07-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2022421952A Pending AU2022421952A1 (en) | 2021-12-22 | 2022-12-22 | Arylsulphonamide compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20250059188A1 (https=) |
| EP (1) | EP4452977A4 (https=) |
| JP (1) | JP2025501767A (https=) |
| KR (1) | KR20240150419A (https=) |
| CN (1) | CN118715222A (https=) |
| AU (1) | AU2022421952A1 (https=) |
| CA (1) | CA3241624A1 (https=) |
| MX (1) | MX2024007885A (https=) |
| WO (1) | WO2023115142A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4452978A4 (en) * | 2021-12-22 | 2025-12-17 | Anaxis Pharma Pty Ltd | BIFUNCTIONAL ARYLSULFONAMIDE COMPOUNDS |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7202363B2 (en) * | 2003-07-24 | 2007-04-10 | Abbott Laboratories | Thienopyridine and furopyridine kinase inhibitors |
| PE20061119A1 (es) * | 2005-01-19 | 2006-11-27 | Aventis Pharma Sa | PIRAZOLO PIRIDINAS SUSTITUIDAS COMO INHIBIDORES DE CINASAS FAK, KDR Y Tie |
| EP1683796A1 (en) * | 2005-01-24 | 2006-07-26 | Schering Aktiengesellschaft | Pyrazolopyridines, their preparation and their medical use |
| TW200815437A (en) * | 2006-06-13 | 2008-04-01 | Bayer Schering Pharma Ag | Substituted aminopyrazolopyridines and salts thereof, pharmaceutical compositions comprising same, methods of preparing same and uses of same |
| WO2018192416A1 (en) * | 2017-04-17 | 2018-10-25 | National Institute Of Biological Sciences, Beijing | Treating Male Senescence |
| DK4168401T3 (da) * | 2020-06-19 | 2026-04-13 | Anaxis Pharma Pty Ltd | Sulfonamidforbindelser |
| EP4452978A4 (en) * | 2021-12-22 | 2025-12-17 | Anaxis Pharma Pty Ltd | BIFUNCTIONAL ARYLSULFONAMIDE COMPOUNDS |
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2022
- 2022-12-22 MX MX2024007885A patent/MX2024007885A/es unknown
- 2022-12-22 US US18/722,104 patent/US20250059188A1/en active Pending
- 2022-12-22 CA CA3241624A patent/CA3241624A1/en active Pending
- 2022-12-22 EP EP22908904.0A patent/EP4452977A4/en active Pending
- 2022-12-22 CN CN202280091908.0A patent/CN118715222A/zh active Pending
- 2022-12-22 JP JP2024538383A patent/JP2025501767A/ja active Pending
- 2022-12-22 KR KR1020247024225A patent/KR20240150419A/ko active Pending
- 2022-12-22 WO PCT/AU2022/051568 patent/WO2023115142A1/en not_active Ceased
- 2022-12-22 AU AU2022421952A patent/AU2022421952A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP4452977A4 (en) | 2025-12-17 |
| KR20240150419A (ko) | 2024-10-15 |
| MX2024007885A (es) | 2024-09-23 |
| JP2025501767A (ja) | 2025-01-23 |
| EP4452977A1 (en) | 2024-10-30 |
| CA3241624A1 (en) | 2023-06-29 |
| US20250059188A1 (en) | 2025-02-20 |
| CN118715222A (zh) | 2024-09-27 |
| WO2023115142A1 (en) | 2023-06-29 |
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Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE NAME OF THE INVENTOR TO READ BRZOZOWSKI, MARTIN; POITEVIN, CHRISTOPHE; GARNIER, JEAN-MARC DANIEL; GARDNER, CHRISTOPHER; LESSENE, GUILLAUME LAURENT; CZABOTAR, PETER EDWARD; SCHUSTER-KLEIN, CAROLE ANNIE; DAVIES, KATHERINE; COWAN, ANGUS AND KERSTEN, WILHELMUS JOHANNES ANTONIUS |