CA2301842C - Substituted benzene compounds as antiproliferative and cholesterol lowering agents - Google Patents
Substituted benzene compounds as antiproliferative and cholesterol lowering agents Download PDFInfo
- Publication number
- CA2301842C CA2301842C CA2301842A CA2301842A CA2301842C CA 2301842 C CA2301842 C CA 2301842C CA 2301842 A CA2301842 A CA 2301842A CA 2301842 A CA2301842 A CA 2301842A CA 2301842 C CA2301842 C CA 2301842C
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- CA
- Canada
- Prior art keywords
- alkyl
- aminosulfonyl
- methoxyphenyl
- ocf3
- compound
- 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.)
- Expired - Fee Related
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- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 34
- 230000001028 anti-proliverative effect Effects 0.000 title description 5
- 239000003529 anticholesteremic agent Substances 0.000 title description 3
- 229940127226 anticholesterol agent Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 239000000203 mixture Substances 0.000 claims abstract description 66
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 14
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 10
- 201000011510 cancer Diseases 0.000 claims abstract description 10
- 208000015181 infectious disease Diseases 0.000 claims abstract description 5
- 208000037803 restenosis Diseases 0.000 claims abstract description 5
- 230000002792 vascular Effects 0.000 claims abstract description 4
- -1 N((C1-C6)alkyl)2 Chemical group 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 40
- 229910052801 chlorine Inorganic materials 0.000 claims description 38
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 37
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical group 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 229910052794 bromium Inorganic materials 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 12
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 6
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- 229940002612 prodrug Drugs 0.000 claims description 5
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- 239000002254 cytotoxic agent Substances 0.000 claims description 2
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 2
- 244000005700 microbiome Species 0.000 claims description 2
- 230000008685 targeting Effects 0.000 claims description 2
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 32
- 125000003118 aryl group Chemical group 0.000 abstract description 13
- 238000011282 treatment Methods 0.000 abstract description 12
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- 238000011161 development Methods 0.000 abstract description 4
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 66
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
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- 101150041968 CDC13 gene Proteins 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 22
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- 125000000217 alkyl group Chemical group 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
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- 238000006243 chemical reaction Methods 0.000 description 14
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 12
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- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 11
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 125000004432 carbon atom Chemical group C* 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 150000003626 triacylglycerols Chemical class 0.000 description 8
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- 125000004429 atom Chemical group 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 7
- RCTCBSDWAUCMEI-UHFFFAOYSA-N 5-bromo-2,3,4-trifluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC(Br)=C(F)C(F)=C1F RCTCBSDWAUCMEI-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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- HIPCPVSKULEHBJ-UHFFFAOYSA-N 2-bromo-3,4,5-trifluoro-n-(3-hydroxy-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(O)C(OC)=CC=C1NS(=O)(=O)C1=CC(F)=C(F)C(F)=C1Br HIPCPVSKULEHBJ-UHFFFAOYSA-N 0.000 description 5
- BLQFHJKRTDIZLX-UHFFFAOYSA-N 5-amino-2-methoxyphenol Chemical compound COC1=CC=C(N)C=C1O BLQFHJKRTDIZLX-UHFFFAOYSA-N 0.000 description 5
- FTIFAPZODKUUQX-UHFFFAOYSA-N 5-bromo-2,3,4-trifluoro-n-(3-hydroxy-4-methoxyphenyl)benzenesulfonamide Chemical compound C1=C(O)C(OC)=CC=C1NS(=O)(=O)C1=CC(Br)=C(F)C(F)=C1F FTIFAPZODKUUQX-UHFFFAOYSA-N 0.000 description 5
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- 229940079593 drug Drugs 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 5
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- 229910052717 sulfur Inorganic materials 0.000 description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 4
- XFTDZYFHXRZLEF-UHFFFAOYSA-N 2,3,4-trifluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C(F)=C1F XFTDZYFHXRZLEF-UHFFFAOYSA-N 0.000 description 4
- IAPZMOXNDIVGNQ-UHFFFAOYSA-N 3-bromo-2,4,5,6-tetrafluoro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=C(F)C(F)=C(F)C(Br)=C1F IAPZMOXNDIVGNQ-UHFFFAOYSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 4
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- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003239 susceptibility assay Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- 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
- C07C311/21—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 a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/917,025 | 1997-08-22 | ||
| US08/917,025 US6284923B1 (en) | 1997-08-22 | 1997-08-22 | Substituted benzene compounds as antiproliferative and cholesterol lowering action |
| PCT/US1998/016781 WO1999010320A1 (en) | 1997-08-22 | 1998-08-13 | Substituted benzene compounds as antiproliferative and cholesterol lowering agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2301842A1 CA2301842A1 (en) | 1999-03-04 |
| CA2301842C true CA2301842C (en) | 2010-04-27 |
Family
ID=25438246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2301842A Expired - Fee Related CA2301842C (en) | 1997-08-22 | 1998-08-13 | Substituted benzene compounds as antiproliferative and cholesterol lowering agents |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US6284923B1 (show.php) |
| EP (1) | EP1005453B1 (show.php) |
| JP (1) | JP4309041B2 (show.php) |
| AT (1) | ATE280756T1 (show.php) |
| AU (1) | AU748826B2 (show.php) |
| CA (1) | CA2301842C (show.php) |
| DE (1) | DE69827267T2 (show.php) |
| ES (1) | ES2245803T3 (show.php) |
| PT (1) | PT1005453E (show.php) |
| WO (1) | WO1999010320A1 (show.php) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2205183T3 (es) * | 1996-02-22 | 2004-05-01 | Tularik, Inc. | Pentafluorobencenosulfonamidas y analogos. |
| DK0939627T3 (da) * | 1996-07-19 | 2003-10-13 | Tularik Inc | Pentaflourbenzensulfonamider og analoger |
| US6583157B2 (en) | 1998-01-29 | 2003-06-24 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| WO1999038845A1 (en) | 1998-01-29 | 1999-08-05 | Tularik Inc. | Ppar-gamma modulators |
| EP1090014B1 (en) * | 1998-06-25 | 2003-09-03 | Tularik Inc. | Arylsulfonanilide phosphates |
| EE200100302A (et) * | 1998-12-02 | 2002-08-15 | Pfizer Products Inc. | Meetodid ja kompositsioonid p53 perekonna valgu konformatsioonilise stabiilsuse taastamiseks |
| US7041691B1 (en) | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| ES2437103T3 (es) * | 1999-06-30 | 2014-01-08 | Amgen Inc. | Compuestos para la modulacion de la actividad de PPAR gamma |
| US6306615B1 (en) | 1999-08-19 | 2001-10-23 | Tularik Inc. | Detection method for monitoring β tubulin isotype specific modification |
| WO2001082916A2 (en) | 2000-05-03 | 2001-11-08 | Tularik Inc. | Combination therapeutic compositions and methods of use |
| US20030171399A1 (en) | 2000-06-28 | 2003-09-11 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| US20050250854A1 (en) * | 2000-11-03 | 2005-11-10 | Amgen Inc. | Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents |
| AU2002234165A1 (en) | 2000-11-03 | 2002-05-27 | Tularik, Inc. | Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents |
| EP1402890B1 (en) * | 2001-06-08 | 2008-01-09 | Institute of Medicinal Molecular Design, Inc. | Sulfonamide derivatives |
| JP2003081937A (ja) * | 2001-09-07 | 2003-03-19 | Bayer Ag | ベンゼンスルホンアミド誘導体 |
| US7833734B2 (en) * | 2002-11-26 | 2010-11-16 | Institute Of Virology Of The Slovak Academy Of Sciences | CA IX-specific inhibitors |
| EP2594265B1 (en) * | 2002-11-26 | 2015-10-28 | Institute Of Virology | Ca ix-specific inhibitors |
| US7223761B2 (en) | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| FI20055498A0 (fi) * | 2005-09-16 | 2005-09-16 | Biotie Therapies Corp | Sulfonamidijohdannaisia |
| GB0526252D0 (en) * | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| JP5860045B2 (ja) | 2010-07-09 | 2016-02-16 | ファイザー・リミテッドＰｆｉｚｅｒ Ｌｉｍｉｔｅｄ | 化合物 |
| US8692001B2 (en) | 2010-10-27 | 2014-04-08 | Dynamix Pharmaceuticals Ltd. | Sulfonamides for the modulation of PKM2 |
| US20150291517A1 (en) * | 2012-11-28 | 2015-10-15 | Martijn Fiers | Benzenesulfonamide compounds for somatic embryogenesis in plants |
| WO2015031220A1 (en) * | 2013-08-28 | 2015-03-05 | Borgwarner Inc. | High temperature valve shaft seal |
| GB201514021D0 (en) | 2015-08-07 | 2015-09-23 | Arner Elias Set Jeno | Novel Pyridines and their use in the treatment of cancer |
| WO2018146471A1 (en) | 2017-02-07 | 2018-08-16 | Oblique Therapeutics Ab | Heterocyclylsulfonyl-substituted pyridines and their use in the treatment of cancer |
| EP3580203A1 (en) | 2017-02-07 | 2019-12-18 | Oblique Therapeutics AB | Hydrocarbylsulfonyl-substituted pyridines and their use in the treatment of cancer |
| WO2018146468A1 (en) | 2017-02-07 | 2018-08-16 | Oblique Therapeutics Ab | Sulfinylpyridines and their use in the treatment of cancer |
| JP2020507625A (ja) | 2017-02-07 | 2020-03-12 | オブリーク セラピューティクス アーベー | ヘテロアリールスルホニル置換ピリジンおよび癌の治療におけるそれらの使用 |
| WO2020097408A1 (en) * | 2018-11-09 | 2020-05-14 | Nimbus Artemis, Inc. | Acly inhibitors and uses thereof |
| US20220281812A1 (en) * | 2019-07-17 | 2022-09-08 | 2692372 Ontario, Inc. | Benzenesulfonamide derivatives and uses thereof |
| EP4496569A1 (en) * | 2022-03-21 | 2025-01-29 | ChemoCentryx, Inc. | Cxcr6 sulfonamide compounds |
| WO2024175999A2 (en) * | 2023-02-23 | 2024-08-29 | Dunad Therapeutics Ltd. | Benzenesulfonamide derivatives and uses thereof |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1955207A (en) | 1931-09-16 | 1934-04-17 | Ig Farbenindustrie Ag | Mothproofing agent |
| DE622494C (de) | 1932-01-03 | 1935-11-29 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Mono- bzw. Polynitropolysulfonen und deren Reduktionsprodukten |
| US2358365A (en) | 1940-08-03 | 1944-09-19 | Parke Davis & Co | Sulphonamide derivatives and process for obtaining the same |
| US2450863A (en) | 1946-03-07 | 1948-10-05 | Socony Vacuum Oil Co Inc | Amides from sulfonyl fluorides |
| CH361275A (de) * | 1957-09-10 | 1962-04-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen Arylsulfonarylamiden |
| US2937202A (en) | 1958-05-19 | 1960-05-17 | Dow Chemical Co | Substituted benzenesulfonanilides |
| GB938890A (en) | 1961-02-03 | 1963-10-09 | Boots Pure Drug Co Ltd | New fungicidal compositions and compounds |
| NL301745A (show.php) | 1962-12-17 | |||
| CH504416A (de) * | 1966-12-05 | 1971-03-15 | Ciba Geigy Ag | Verfahren zur Herstellung von aromatischen Sulfamoylverbindungen |
| US3505455A (en) | 1966-12-15 | 1970-04-07 | Ansul Co | Nematocidal method |
| NL174644C (nl) | 1970-04-13 | 1984-07-16 | Minnesota Mining & Mfg | Werkwijze ter bereiding van een herbicide verbinding; tevens werkwijze voor de bereiding van een preparaat met herbicide werking. |
| US3951910A (en) * | 1973-12-28 | 1976-04-20 | General Electric Company | Flame retardant polycarbonate composition |
| US4013621A (en) | 1975-04-29 | 1977-03-22 | Ciba-Geigy Corporation | Substituted sulfonamide derivatives of hindered phenols and stabilized compositions |
| DE2528697C2 (de) | 1975-06-27 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Salicylaldehyden |
| US4034110A (en) | 1976-09-20 | 1977-07-05 | Hoffmann-La Roche Inc. | Anthelmintics effective against liver flukes |
| US4239699A (en) | 1978-05-24 | 1980-12-16 | Henkel Corporation | Sulfonamidophenols, metal complexes thereof, and solutions containing such compounds for use in extraction of metal values |
| US4373017A (en) | 1980-03-05 | 1983-02-08 | Konishiroku Photo Industry Co., Ltd. | Photosensitive compound and photosensitive material containing it |
| US4483986A (en) | 1982-05-03 | 1984-11-20 | Eli Lilly And Company | 4-Nitrobenzophenone compounds |
| NZ215272A (en) | 1985-02-27 | 1989-08-29 | Mitsui Toatsu Chemicals | Fungicidal n-(2-chloro-4-nitrophenyl)-benzenesulphonamide derivatives and compositions thereof |
| US4692466A (en) | 1985-02-28 | 1987-09-08 | Mitsui Toatsu Chemicals, Incorporated | N-(2-chloro-4-trifluoromethylphenyl)-3-trifluoromethylbenzenesulfonamide derivative and agricultural fungicide containing same |
| US5280043A (en) | 1988-10-10 | 1994-01-18 | Smith Kline & French Laboratories Ltd. | Sulphonamido containing phenylalkanoic acids as thromboxane A2 antagonists |
| DE3905075A1 (de) | 1989-02-18 | 1990-08-30 | Hoechst Ag | Benzolsulfonamide und verfahren zu ihrer herstellung |
| DE69129611T2 (de) | 1990-08-20 | 1998-12-17 | Eisai Co., Ltd., Tokio/Tokyo | Sulfonamid-Derivate |
| AU6112896A (en) * | 1995-06-07 | 1996-12-30 | Sugen, Inc. | Tyrphostin-like compounds for the treatment of cell prolifer ative disorders or cell differentiation disorders |
-
1997
- 1997-08-22 US US08/917,025 patent/US6284923B1/en not_active Expired - Fee Related
-
1998
- 1998-08-13 ES ES98939384T patent/ES2245803T3/es not_active Expired - Lifetime
- 1998-08-13 AU AU87824/98A patent/AU748826B2/en not_active Ceased
- 1998-08-13 EP EP98939384A patent/EP1005453B1/en not_active Expired - Lifetime
- 1998-08-13 WO PCT/US1998/016781 patent/WO1999010320A1/en not_active Ceased
- 1998-08-13 CA CA2301842A patent/CA2301842C/en not_active Expired - Fee Related
- 1998-08-13 AT AT98939384T patent/ATE280756T1/de not_active IP Right Cessation
- 1998-08-13 DE DE69827267T patent/DE69827267T2/de not_active Expired - Lifetime
- 1998-08-13 JP JP2000507650A patent/JP4309041B2/ja not_active Expired - Fee Related
- 1998-08-13 PT PT98939384T patent/PT1005453E/pt unknown
-
2001
- 2001-05-31 US US09/872,463 patent/US6388131B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1005453B1 (en) | 2004-10-27 |
| US6284923B1 (en) | 2001-09-04 |
| AU748826B2 (en) | 2002-06-13 |
| JP2001514167A (ja) | 2001-09-11 |
| PT1005453E (pt) | 2005-02-28 |
| WO1999010320A1 (en) | 1999-03-04 |
| US6388131B2 (en) | 2002-05-14 |
| ES2245803T3 (es) | 2006-01-16 |
| AU8782498A (en) | 1999-03-16 |
| DE69827267T2 (de) | 2006-02-02 |
| JP4309041B2 (ja) | 2009-08-05 |
| US20020013496A1 (en) | 2002-01-31 |
| CA2301842A1 (en) | 1999-03-04 |
| DE69827267D1 (de) | 2004-12-02 |
| ATE280756T1 (de) | 2004-11-15 |
| EP1005453A1 (en) | 2000-06-07 |
| WO1999010320A8 (en) | 1999-09-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |