CA2733390A1 - Methionine analogs and methods of using same - Google Patents
Methionine analogs and methods of using same Download PDFInfo
- Publication number
- CA2733390A1 CA2733390A1 CA2733390A CA2733390A CA2733390A1 CA 2733390 A1 CA2733390 A1 CA 2733390A1 CA 2733390 A CA2733390 A CA 2733390A CA 2733390 A CA2733390 A CA 2733390A CA 2733390 A1 CA2733390 A1 CA 2733390A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- compound
- optionally substituted
- cycloalkyl
- heterocycloalkyl
- 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.)
- Abandoned
Links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/10—Antimycotics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/66—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfo, esterified sulfo or halosulfonyl groups, bound to the carbon skeleton
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Virology (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)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8555608P | 2008-08-01 | 2008-08-01 | |
| US61/085,556 | 2008-08-01 | ||
| PCT/US2009/052474 WO2010014943A2 (en) | 2008-08-01 | 2009-07-31 | Methionine analogs and methods of using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2733390A1 true CA2733390A1 (en) | 2010-02-04 |
Family
ID=41414372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2733390A Abandoned CA2733390A1 (en) | 2008-08-01 | 2009-07-31 | Methionine analogs and methods of using same |
Country Status (8)
| Country | Link |
|---|---|
| US (5) | US8580859B2 (https=) |
| EP (1) | EP2326619B1 (https=) |
| JP (1) | JP5650642B2 (https=) |
| CN (1) | CN102171185A (https=) |
| AU (1) | AU2009276343A1 (https=) |
| CA (1) | CA2733390A1 (https=) |
| IL (1) | IL210956A0 (https=) |
| WO (1) | WO2010014943A2 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102171185A (zh) | 2008-08-01 | 2011-08-31 | 拜奥西尼斯医药股份有限公司 | 甲硫氨酸类似物及其使用方法 |
| US9200251B1 (en) | 2011-03-31 | 2015-12-01 | David Gordon Bermudes | Bacterial methionine analogue and methionine synthesis inhibitor anticancer, antiinfective and coronary heart disease protective microcins and methods of treatment therewith |
| WO2019169029A1 (en) | 2018-02-28 | 2019-09-06 | Bioxiness Pharmaceuticals, Inc. | Target specific chemotherapeutic agents |
Family Cites Families (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR961832A (https=) | 1943-03-20 | 1950-05-23 | ||
| CH254537A (de) | 1947-12-18 | 1948-05-15 | Ag Sandoz | Verfahren zur Herstellung eines neuen kapillaraktiven Stoffes. |
| DE1020144B (de) | 1956-07-02 | 1957-11-28 | Dehydag Gmbh | Wasch- und Reinigungsmittel |
| FR1390191A (fr) | 1963-07-19 | 1965-02-26 | Dehydag Gmbh | Procédé de préparation de sulfobétaïnes à bases hétérocycliques de type aromatique |
| US3519683A (en) | 1967-03-31 | 1970-07-07 | Meiji Seika Co | Process for preparing 5-amino-5-deoxy-d-glucose-1-sulfonic acid |
| GB1580899A (en) | 1976-07-27 | 1980-12-10 | Fujisawa Pharmaceutical Co | Hydroxyaminohydrocarbonphosphonic acid derivatives and production and use thereof |
| JPS5463024A (en) | 1977-10-27 | 1979-05-21 | Fujisawa Pharmaceut Co Ltd | 3-(n-formyl-n-hydroxyamino)-2(r)-hydroxypropyl-phosphonic acid, its preparation, and its use |
| US4169950A (en) | 1977-12-08 | 1979-10-02 | Research Organics | Amino-hydroxy-alkyl sulfonic acid zwitterions |
| IL61985A0 (en) | 1980-02-01 | 1981-02-27 | Sparamedica Ag | Phosphinic and phosphonic acid derivatives,their manufacture and pharmaceutical compositions containing them |
| DE3273586D1 (en) | 1981-11-02 | 1986-11-06 | Ici Plc | Substituted propyl phosphonic acid derivatives, their use as herbicides, herbicidal compositions containing them, and methods of preparing them |
| DE3245887A1 (de) | 1982-12-11 | 1984-06-14 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung substituierter phosphon und phosphinsaeuren |
| GB8308506D0 (en) | 1983-03-28 | 1983-05-05 | Ici Plc | Heterocyclic compounds |
| GB8410989D0 (en) | 1984-04-30 | 1984-06-06 | Ici Plc | Heterocyclic compounds |
| DE3435156A1 (de) | 1984-09-25 | 1986-04-03 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur herstellung der stereoisomeren von 1-amino-alkylphosphonsaeuren oder 1-aminoalkylphosphinsaeuren |
| JPS62215597A (ja) | 1986-03-14 | 1987-09-22 | Mitsubishi Chem Ind Ltd | β−メルカプト−α−アミノエチルホスホン酸誘導体 |
| IT1211792B (it) | 1987-09-21 | 1989-11-03 | Sigma Tau Ind Farmaceuti | O-alcanoil derivati dell'acido 3ammino-2-idrossipropansolfonico adattivita'anticonvulsivante e loro composizioni farmaceutiche per il trattamento terapeutico dell'epilessia |
| GB8727792D0 (en) | 1987-11-27 | 1987-12-31 | Merck Sharp & Dohme | Therapeutic agents |
| SE8801729D0 (sv) | 1988-05-06 | 1988-05-06 | Astra Ab | Purine derivatives for use in therapy |
| JP2733511B2 (ja) | 1988-10-22 | 1998-03-30 | 日本臓器製薬株式会社 | 新規アミノアルカン誘導体 |
| JP3174566B2 (ja) | 1990-04-20 | 2001-06-11 | 日本臓器製薬株式会社 | アミノアルカン誘導体 |
| DE69125216T2 (de) * | 1990-07-19 | 1997-09-25 | Nippon Zoki Pharmaceutical Co | Aminoalkanesulfonsäurederivate und pharmazeutische Zusammensetzungen davon zur Prävention oder Behandlung von Herzerkrankungen |
| JP2724906B2 (ja) | 1990-07-19 | 1998-03-09 | 日本臓器製薬株式会社 | 新規フェニルアラニルアミノアルカン誘導体 |
| DE4124004C2 (de) | 1991-07-19 | 1995-01-26 | Hell Ag Linotype | Vorrichtung zum Auf- und Abspannen von Filmmaterial und Betriebsweise der Vorrichtung |
| GB9122859D0 (en) * | 1991-10-28 | 1991-12-11 | Smithkline Beecham Plc | Novel compounds |
| JPH07116382B2 (ja) | 1992-01-28 | 1995-12-13 | 株式会社同仁化学研究所 | 水溶性メチレンビスジアルキルアニリン誘導体及びその塩類並びにそれらを用いた過酸化物質定量用組成物 |
| GB9202779D0 (en) | 1992-02-10 | 1992-03-25 | Ici Plc | Novel compounds |
| US5760021A (en) | 1992-05-29 | 1998-06-02 | The Procter & Gamble Company | Phosphonocarboxylate compounds pharmaceutical compositions, and methods for treating abnormal calcium and phosphate metabolism |
| JP3526575B2 (ja) * | 1993-03-08 | 2004-05-17 | エーザイ株式会社 | ホスホン酸誘導体 |
| CA2118985A1 (en) * | 1993-04-02 | 1994-10-03 | Dinesh V. Patel | Heterocyclic inhibitors of farnesyl protein transferase |
| WO1995001955A1 (en) | 1993-07-09 | 1995-01-19 | Kao Corporation | 2-hydroxypropanediamine derivative and detergent composition containing the same |
| US5658749A (en) | 1994-04-05 | 1997-08-19 | Corning Clinical Laboratories, Inc. | Method for processing mycobacteria |
| JPH09316474A (ja) | 1996-05-24 | 1997-12-09 | Hitachi Maxell Ltd | 潤滑性物質およびこの潤滑性物質を用いた磁気記録媒体 |
| WO1998015525A1 (en) | 1996-10-07 | 1998-04-16 | Sumitomo Pharmaceuticals Co., Ltd. | Hydroxamic acids |
| CZ141399A3 (cs) | 1996-10-24 | 1999-07-14 | Novartis Ag | Substituované aminoalkanfosfonové kyseliny, způsob jejich přípravy a farmaceutické prostředky, které je obsahují |
| US6172057B1 (en) * | 1997-02-27 | 2001-01-09 | American Cyanamid Company | N-Hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors |
| KR100352316B1 (ko) * | 1997-07-31 | 2002-09-12 | 더 프록터 앤드 갬블 캄파니 | 메탈로프로테아제억제제로서사용되는술포닐아미노치환히드록삼산유도체 |
| US6403632B1 (en) * | 2000-03-01 | 2002-06-11 | Bristol Myers Squibb Pharma Co | Lactam metalloprotease inhibitors |
| ZA988967B (en) * | 1997-10-03 | 2000-04-03 | Du Pont Pharm Co | Lactam metalloprotease inhibitors. |
| IT1299266B1 (it) * | 1998-05-15 | 2000-02-29 | Sigma Tau Ind Farmaceuti | Inibitori reversibili della carnitina palmitoil trasferasi |
| FR2780402B1 (fr) | 1998-06-30 | 2001-04-27 | Adir | Nouveaux composes acides carboxyliques et hydroxamiques inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| KR20010080709A (ko) | 1998-12-10 | 2001-08-22 | 프리돌린 클라우스너, 롤란드 비. 보레르 | 프로콜라겐 ｃ-프로티나제 저해제 |
| FR2788526B1 (fr) | 1999-01-20 | 2002-07-05 | Inst Nat Sante Rech Med | Composes tripeptidiques utiles a titre d'hinhibiteurs selectifs de l'aminopeptidase a et compositions pharmaceutiques correspondantes |
| EP1165500A1 (en) * | 1999-04-02 | 2002-01-02 | Du Pont Pharmaceuticals Company | Amide derivatives as inhibitors of matrix metalloproteinases,tnf-alpha,and aggrecanase |
| FR2791982B1 (fr) | 1999-04-06 | 2002-12-27 | Inst Nat Sante Rech Med | Inhibiteurs de lta4 hydrolase et leurs applications therapeutiques. |
| AU4249700A (en) | 1999-04-19 | 2000-11-02 | Sumitomo Pharmaceuticals Company, Limited | Hydroxamic acid derivative |
| AU5994900A (en) * | 1999-07-09 | 2001-01-30 | Isis Innovation Limited | Compounds for inhibiting diseases and preparing cells for transplantation |
| JP4153647B2 (ja) | 2000-04-05 | 2008-09-24 | 三菱重工業株式会社 | フェントン反応抑制剤および一重項酸素産生抑制剤 |
| WO2001093872A1 (de) | 2000-06-08 | 2001-12-13 | Jomaa Pharmaka Gmbh | Verwendung von phosphororganischen hydroxamsäurederivaten zur herstellung von arzneimitteln |
| WO2002018395A1 (en) * | 2000-08-31 | 2002-03-07 | Merck & Co., Inc. | Phosphate derivatives as immunoregulatory agents |
| AU2002230385A1 (en) * | 2000-09-25 | 2002-04-15 | Questcor Pharmaceuticals, Inc. | Peptide deformylase inhibitors |
| EP1361872A4 (en) * | 2000-10-03 | 2004-05-19 | Univ Virginia | NOVEL LYSOPHOSPHATIDIC ACID RECEPTOR AGONISTS AND ANTAGONISTS |
| FR2816837A1 (fr) | 2000-11-17 | 2002-05-24 | Oreal | Utilisation d'au moins un derive amino sulfonique dans une composition destinee a favoriser la desquamation de la peau |
| FR2821621B1 (fr) | 2001-03-05 | 2004-11-05 | Oreal | Polyurethannes anioniques a caractere elastique et leur utilisation dans des compositions cosmetiques |
| US20050070506A1 (en) | 2002-01-18 | 2005-03-31 | Doherty George A. | Selective s1p1/edg1 receptor agonists |
| CA2851462A1 (en) * | 2003-01-08 | 2004-07-29 | University Of Washington | Antibacterial agents |
| US7456157B2 (en) | 2003-02-18 | 2008-11-25 | Kyorin Pharmaceutical Co., Ltd. | Aminophosphonic acid derivatives, addition salts thereof and S1P receptor modulators |
| JP5146714B2 (ja) | 2003-06-23 | 2013-02-20 | ビーエイチアイ リミテッド パートナーシップ | アミロイド関連疾患を治療するための方法および組成物 |
| FR2858617A1 (fr) | 2003-08-06 | 2005-02-11 | Inst Nat Sante Rech Med | Derives de 4',4'-dithiobis-(3-aminobutane-1-sulfonate-1- sulfonates) nouveaux et compositions les contenant |
| WO2005020973A2 (en) | 2003-08-29 | 2005-03-10 | The University Of Houston System | Compositions having antimycrobial activity including a hydroxamate or a hydroxamate and a hydroxylamine |
| US20050107447A1 (en) | 2003-11-03 | 2005-05-19 | Lynch Kevin R. | Novel lysophosphatidic acid receptor agonists and antagonists |
| JP4182910B2 (ja) | 2004-03-30 | 2008-11-19 | ダイソー株式会社 | スフィンゴミエリン類縁体とその製造法 |
| US20060183800A1 (en) | 2004-11-12 | 2006-08-17 | Xianqi Kong | Methods and fluorinated compositions for treating amyloid-related diseases |
| WO2006085149A2 (en) * | 2004-12-22 | 2006-08-17 | Neurochem (International) Limited | Methods and compositions for treating amyloid-related diseases |
| DK2839830T3 (da) * | 2005-01-14 | 2019-08-19 | Urigen Inc | Kits og sammensætninger til behandling af lidelser i de nedre urinveje |
| JP2006257069A (ja) | 2005-02-17 | 2006-09-28 | Kemikurea:Kk | 蛍光標識化スフィンゴシン１−リン酸メチレン置換体およびリン酸アルケニル置換体 |
| WO2007069020A2 (en) * | 2005-12-15 | 2007-06-21 | Vicuron Pharmaceuticals Inc. | N-hydroxyamide derivatives possessing antibacterial activity |
| AU2008333929A1 (en) | 2007-12-03 | 2009-06-11 | Signum Biosciences, Inc. | Acid mimic compounds for the inhibition of isoprenyl-S-cysteinyl methyltransferase |
| CN102171185A (zh) | 2008-08-01 | 2011-08-31 | 拜奥西尼斯医药股份有限公司 | 甲硫氨酸类似物及其使用方法 |
-
2009
- 2009-07-31 CN CN2009801390134A patent/CN102171185A/zh active Pending
- 2009-07-31 CA CA2733390A patent/CA2733390A1/en not_active Abandoned
- 2009-07-31 AU AU2009276343A patent/AU2009276343A1/en not_active Abandoned
- 2009-07-31 JP JP2011521364A patent/JP5650642B2/ja not_active Expired - Fee Related
- 2009-07-31 EP EP09791073.1A patent/EP2326619B1/en not_active Not-in-force
- 2009-07-31 WO PCT/US2009/052474 patent/WO2010014943A2/en not_active Ceased
- 2009-07-31 US US13/056,102 patent/US8580859B2/en not_active Expired - Fee Related
-
2011
- 2011-01-30 IL IL210956A patent/IL210956A0/en unknown
-
2013
- 2013-10-07 US US14/047,845 patent/US20140142189A1/en not_active Abandoned
-
2014
- 2014-12-10 US US14/565,970 patent/US20150329481A1/en not_active Abandoned
-
2016
- 2016-02-26 US US15/054,761 patent/US9695119B2/en not_active Expired - Fee Related
-
2017
- 2017-06-01 US US15/611,575 patent/US20170267632A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20110196014A1 (en) | 2011-08-11 |
| JP2011529921A (ja) | 2011-12-15 |
| EP2326619B1 (en) | 2019-02-27 |
| WO2010014943A2 (en) | 2010-02-04 |
| IL210956A0 (en) | 2011-04-28 |
| WO2010014943A3 (en) | 2011-01-13 |
| US20170267632A1 (en) | 2017-09-21 |
| US8580859B2 (en) | 2013-11-12 |
| US9695119B2 (en) | 2017-07-04 |
| US20140142189A1 (en) | 2014-05-22 |
| JP5650642B2 (ja) | 2015-01-07 |
| CN102171185A (zh) | 2011-08-31 |
| EP2326619A2 (en) | 2011-06-01 |
| US20170029369A1 (en) | 2017-02-02 |
| US20150329481A1 (en) | 2015-11-19 |
| AU2009276343A1 (en) | 2010-02-04 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20150731 |