AU748826B2 - Substituted benzene compounds as antiproliferative and cholesterol lowering agents - Google Patents
Substituted benzene compounds as antiproliferative and cholesterol lowering agents Download PDFInfo
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- AU748826B2 AU748826B2 AU87824/98A AU8782498A AU748826B2 AU 748826 B2 AU748826 B2 AU 748826B2 AU 87824/98 A AU87824/98 A AU 87824/98A AU 8782498 A AU8782498 A AU 8782498A AU 748826 B2 AU748826 B2 AU 748826B2
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- Prior art keywords
- compound
- compounds
- substituted
- cholesterol
- aminosulfonyl
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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
- C07C311/15—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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Diabetes (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 |
|---|---|---|---|
| US08/917025 | 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 |
|---|---|
| AU8782498A AU8782498A (en) | 1999-03-16 |
| AU748826B2 true AU748826B2 (en) | 2002-06-13 |
Family
ID=25438246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU87824/98A Ceased AU748826B2 (en) | 1997-08-22 | 1998-08-13 | Substituted benzene compounds as antiproliferative and cholesterol lowering agents |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US6284923B1 (enExample) |
| EP (1) | EP1005453B1 (enExample) |
| JP (1) | JP4309041B2 (enExample) |
| AT (1) | ATE280756T1 (enExample) |
| AU (1) | AU748826B2 (enExample) |
| CA (1) | CA2301842C (enExample) |
| DE (1) | DE69827267T2 (enExample) |
| ES (1) | ES2245803T3 (enExample) |
| PT (1) | PT1005453E (enExample) |
| WO (1) | WO1999010320A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3421349B2 (ja) * | 1996-02-22 | 2003-06-30 | テュラリク インコーポレイテッド | ペンタフルオロベンゼンスルホンアミドおよび類縁体 |
| AU710173B2 (en) * | 1996-07-19 | 1999-09-16 | Tularik Inc. | Pentafluorobenzenesulfonamides and analogs |
| US6583157B2 (en) | 1998-01-29 | 2003-06-24 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| ES2317688T3 (es) | 1998-01-29 | 2009-04-16 | Amgen Inc. | Moduladores ppar-gamma. |
| WO1999067258A1 (en) * | 1998-06-25 | 1999-12-29 | Tularik Inc. | Arylsulfonanilide phosphates |
| EA003326B1 (ru) * | 1998-12-02 | 2003-04-24 | Пфайзер Продактс Инк. | Способ лечения рака |
| 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 |
| AU6118001A (en) | 2000-05-03 | 2001-11-12 | Tularik Inc | Combination therapeutic compositions and methods of use |
| US20030171399A1 (en) | 2000-06-28 | 2003-09-11 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| US6822001B2 (en) | 2000-11-03 | 2004-11-23 | Tularik Inc. | Combination therapy using pentafluorobenzenesulfonamides and antineoplastic agents |
| US20050250854A1 (en) * | 2000-11-03 | 2005-11-10 | Amgen 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 |
| WO2004048544A2 (en) * | 2002-11-26 | 2004-06-10 | Bayer Healthcare | 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 |
| WO2014083384A1 (en) * | 2012-11-28 | 2014-06-05 | Stichting Dienst Landbouwkundig Onderzoek | Benzenesulfonamide compounds for somatic embryogenesis iν plants |
| CN105452745B (zh) * | 2013-08-28 | 2019-03-19 | 博格华纳公司 | 高温阀轴密封 |
| GB201514021D0 (en) | 2015-08-07 | 2015-09-23 | Arner Elias Set Jeno | Novel Pyridines 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 |
| CA3051538A1 (en) | 2017-02-07 | 2018-08-16 | Oblique Therapeutics Ab | Heterocyclylsulfonyl-substituted pyridines and their use in the treatment of cancer |
| MA47458A (fr) | 2017-02-07 | 2019-12-18 | Oblique Therapeutics Ab | Pyridines à substitution hydrocarbylsulfonyle et leur utilisation dans le traitement du cancer |
| KR20190115011A (ko) | 2017-02-07 | 2019-10-10 | 오블리크 세러퓨틱스 에이비 | 설피닐피리딘 및 암의 치료에서 이의 용도 |
| US11555012B2 (en) * | 2018-11-09 | 2023-01-17 | Nimbus Artemis, Inc. | ACLY inhibitors and uses thereof |
| WO2021009568A1 (en) * | 2019-07-17 | 2021-01-21 | 2692372 Ontario, Inc. | Benzenesulfonamide derivatives and uses thereof |
| WO2023183763A1 (en) * | 2022-03-21 | 2023-09-28 | Chemocentryx, Inc. | Cxcr6 sulfonamide compounds |
| WO2024175999A2 (en) * | 2023-02-23 | 2024-08-29 | Dunad Therapeutics Ltd. | Benzenesulfonamide derivatives and uses thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB859345A (en) * | 1957-09-10 | 1961-01-18 | Geigy Ag J R | Process for the production of new aryl sulphonic acid arylamides |
| US5143937A (en) * | 1989-02-18 | 1992-09-01 | Hoechst Aktiengesellschaft | Benzenesulfonamides and a process for their preparation |
Family Cites Families (22)
| 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 |
| 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 (enExample) | 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 |
| ATE167473T1 (de) | 1990-08-20 | 1998-07-15 | Eisai Co Ltd | Sulfonamid-derivate |
| WO1996040629A1 (en) * | 1995-06-07 | 1996-12-19 | Sugen, Inc. | Tyrphostin-like compounds for the treatment of cell proliferative 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 CA CA2301842A patent/CA2301842C/en not_active Expired - Fee Related
- 1998-08-13 PT PT98939384T patent/PT1005453E/pt unknown
- 1998-08-13 JP JP2000507650A patent/JP4309041B2/ja not_active Expired - Fee Related
- 1998-08-13 AT AT98939384T patent/ATE280756T1/de not_active IP Right Cessation
- 1998-08-13 WO PCT/US1998/016781 patent/WO1999010320A1/en not_active Ceased
- 1998-08-13 EP EP98939384A patent/EP1005453B1/en not_active Expired - Lifetime
- 1998-08-13 AU AU87824/98A patent/AU748826B2/en not_active Ceased
- 1998-08-13 DE DE69827267T patent/DE69827267T2/de not_active Expired - Lifetime
- 1998-08-13 ES ES98939384T patent/ES2245803T3/es not_active Expired - Lifetime
-
2001
- 2001-05-31 US US09/872,463 patent/US6388131B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB859345A (en) * | 1957-09-10 | 1961-01-18 | Geigy Ag J R | Process for the production of new aryl sulphonic acid arylamides |
| US5143937A (en) * | 1989-02-18 | 1992-09-01 | Hoechst Aktiengesellschaft | Benzenesulfonamides and a process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| PT1005453E (pt) | 2005-02-28 |
| JP2001514167A (ja) | 2001-09-11 |
| WO1999010320A8 (en) | 1999-09-23 |
| US6388131B2 (en) | 2002-05-14 |
| ES2245803T3 (es) | 2006-01-16 |
| DE69827267D1 (de) | 2004-12-02 |
| US20020013496A1 (en) | 2002-01-31 |
| CA2301842A1 (en) | 1999-03-04 |
| ATE280756T1 (de) | 2004-11-15 |
| EP1005453B1 (en) | 2004-10-27 |
| EP1005453A1 (en) | 2000-06-07 |
| JP4309041B2 (ja) | 2009-08-05 |
| WO1999010320A1 (en) | 1999-03-04 |
| US6284923B1 (en) | 2001-09-04 |
| CA2301842C (en) | 2010-04-27 |
| DE69827267T2 (de) | 2006-02-02 |
| AU8782498A (en) | 1999-03-16 |
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Legal Events
| Date | Code | Title | Description |
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| FGA | Letters patent sealed or granted (standard patent) |