WO2006017351A1 - Prodrugs of propofol, compositions and uses thereof - Google Patents

Prodrugs of propofol, compositions and uses thereof Download PDF

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Publication number
WO2006017351A1
WO2006017351A1 PCT/US2005/024907 US2005024907W WO2006017351A1 WO 2006017351 A1 WO2006017351 A1 WO 2006017351A1 US 2005024907 W US2005024907 W US 2005024907W WO 2006017351 A1 WO2006017351 A1 WO 2006017351A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
diisopropyl
amino
compound
hydrogen
Prior art date
Application number
PCT/US2005/024907
Other languages
English (en)
French (fr)
Inventor
Feng Xu
Mark A. Gallop
Original Assignee
Xenoport, Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Xenoport, Inc. filed Critical Xenoport, Inc.
Publication of WO2006017351A1 publication Critical patent/WO2006017351A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound 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
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
    • C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/52—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
PCT/US2005/024907 2004-07-12 2005-07-12 Prodrugs of propofol, compositions and uses thereof WO2006017351A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US58746904P 2004-07-12 2004-07-12
US60/587,469 2004-07-12

Publications (1)

Publication Number Publication Date
WO2006017351A1 true WO2006017351A1 (en) 2006-02-16

Family

ID=35106907

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/024907 WO2006017351A1 (en) 2004-07-12 2005-07-12 Prodrugs of propofol, compositions and uses thereof

Country Status (2)

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US (2) US7241807B2 (US07645792-20100112-C00013.png)
WO (1) WO2006017351A1 (US07645792-20100112-C00013.png)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007131070A2 (en) * 2006-05-04 2007-11-15 Xenoport, Inc. Compositions, dosage forms and methods of treating emesis
WO2008157627A1 (en) * 2007-06-21 2008-12-24 Xenoport, Inc. Use of propofol prodrugs for treating alcohol withdrawal, central pain, anxiety or pruritus
WO2009036322A1 (en) * 2007-09-14 2009-03-19 Xenoport, Inc. Use of propofol prodrugs for treating neuropathic pain
JP2010501504A (ja) * 2006-08-24 2010-01-21 バイエル・シェーリング・ファルマ・アクチェンゲゼルシャフト アミノアシルプロドラッグ誘導体および血栓塞栓性障害の処置用の医薬
CN102381997A (zh) * 2011-09-08 2012-03-21 四川大学华西医院 带有氨基酸酯末端的丙泊酚羟基酸酯类化合物及其制备方法和应用
US8217005B2 (en) 2006-05-26 2012-07-10 Signature Therapeutics, Inc. Controlled release of phenolic opioids
US9023860B2 (en) 2007-11-26 2015-05-05 Signature Therapeutics, Inc. Pro-drugs for controlled release of biologically active compounds
EP2586768A4 (en) * 2010-06-23 2015-07-29 West China Hospital Sichuan Univ HYDROXYACID COMPOUND OF SUBSTITUTED PHENYL ESTER, PREPARATION METHOD THEREOF AND MEDICAL USE THEREOF
US20170050920A1 (en) * 2014-02-17 2017-02-23 Jiangsu Nhwaluokang Phrmceutical Research And Development Co., Ltd Water-soluble propofol derivatives and uses thereof
CN108558685A (zh) * 2017-06-08 2018-09-21 西安力邦制药有限公司 2,6-二取代苯酚葡甲胺类衍生物及应用
WO2021078073A1 (zh) * 2019-10-22 2021-04-29 四川大学华西医院 一类取代苯酚羟基酸酯含n衍生物、制备和用途
WO2022133687A1 (zh) * 2020-12-21 2022-06-30 加拿大力邦制药有限公司 一种药物偶联物、及其制备方法和用途
US11439653B1 (en) 2021-03-30 2022-09-13 Epalex Corporation Fospropofol formulations
US11478490B1 (en) 2021-03-30 2022-10-25 Epalex Corporation Fospropofol formulations
US11547714B2 (en) 2020-02-05 2023-01-10 Epalex Corporation Fospropofol salts, methods and compositions
US11628178B2 (en) 2019-03-26 2023-04-18 Epalex Corporation Fospropofol methods and compositions

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US7250412B2 (en) * 2003-10-24 2007-07-31 Auspex Pharmaceuticals, Inc. PH sensitive prodrugs of 2,6-Diisopropylphenol
WO2006017351A1 (en) * 2004-07-12 2006-02-16 Xenoport, Inc. Prodrugs of propofol, compositions and uses thereof
CA2586410A1 (en) * 2004-12-23 2006-07-06 Xenoport, Inc. Serine amino acid derived prodrugs of propofol, compositions, uses and crystalline forms thereof
US7589239B2 (en) * 2005-09-02 2009-09-15 Auspex Pharmaceuticals Therapeutic agents for the treatment of cancer, metabolic diseases and skin disorders
WO2008052044A2 (en) * 2006-10-26 2008-05-02 Xenoport, Inc. Use of derivatives of propofol for treating diseases associated with oxidative stress
RU2470907C2 (ru) 2007-05-09 2012-12-27 Сигничер Терапьютикс, Инк. Терапевтические соединения
DK2146946T3 (da) 2007-05-09 2011-02-14 Pharmacofore Inc (-)-stereoisomer af 2,6-di-sec-butylphenol og analoger deraf
US20120316247A1 (en) * 2009-10-20 2012-12-13 The General Hospital Corporation Prevention and treatment of post-operative cognitive dysfunction (pocd)
EP2530072A1 (en) 2011-06-03 2012-12-05 Lacer, S.A. New compounds, synthesis and use thereof in the treatment of pain
WO2013093931A2 (en) * 2011-09-19 2013-06-27 Sun Pharma Advanced Research Company Ltd. Novel prodrugs of phenolic drugs
CN102617448B (zh) * 2012-03-13 2014-10-15 四川大学华西医院 4-甲氧甲基-4-(n-丙酰基)苯胺哌啶类化合物、制备方法及用途

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WO1999058555A2 (en) * 1998-05-08 1999-11-18 Vyrex Corporation Water-soluble pro-drugs of 2,6-diisopropylphenol analogues
WO2000048572A1 (en) * 1999-02-18 2000-08-24 Supergen, Inc Phosphocholine linked prodrug derivatives
WO2004033424A1 (en) * 2002-10-08 2004-04-22 Fresenius Kabi Deutschland Gmbh Watersoluble prodrugs of propofol

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WO2008052044A2 (en) * 2006-10-26 2008-05-02 Xenoport, Inc. Use of derivatives of propofol for treating diseases associated with oxidative stress

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007131070A3 (en) * 2006-05-04 2008-04-03 Xenoport Inc Compositions, dosage forms and methods of treating emesis
WO2007131070A2 (en) * 2006-05-04 2007-11-15 Xenoport, Inc. Compositions, dosage forms and methods of treating emesis
US8921418B2 (en) 2006-05-26 2014-12-30 Signature Therapeutics, Inc. Controlled release of phenolic opioids
US8217005B2 (en) 2006-05-26 2012-07-10 Signature Therapeutics, Inc. Controlled release of phenolic opioids
JP2010501504A (ja) * 2006-08-24 2010-01-21 バイエル・シェーリング・ファルマ・アクチェンゲゼルシャフト アミノアシルプロドラッグ誘導体および血栓塞栓性障害の処置用の医薬
WO2008157627A1 (en) * 2007-06-21 2008-12-24 Xenoport, Inc. Use of propofol prodrugs for treating alcohol withdrawal, central pain, anxiety or pruritus
WO2009036322A1 (en) * 2007-09-14 2009-03-19 Xenoport, Inc. Use of propofol prodrugs for treating neuropathic pain
US9023860B2 (en) 2007-11-26 2015-05-05 Signature Therapeutics, Inc. Pro-drugs for controlled release of biologically active compounds
EP2586768A4 (en) * 2010-06-23 2015-07-29 West China Hospital Sichuan Univ HYDROXYACID COMPOUND OF SUBSTITUTED PHENYL ESTER, PREPARATION METHOD THEREOF AND MEDICAL USE THEREOF
CN102381997A (zh) * 2011-09-08 2012-03-21 四川大学华西医院 带有氨基酸酯末端的丙泊酚羟基酸酯类化合物及其制备方法和应用
US20170050920A1 (en) * 2014-02-17 2017-02-23 Jiangsu Nhwaluokang Phrmceutical Research And Development Co., Ltd Water-soluble propofol derivatives and uses thereof
US9643917B2 (en) * 2014-02-17 2017-05-09 Jiangsu Nhwaluokang Pharmceutical Research And Development Co., Ltd Water-soluble propofol derivatives and uses thereof
CN108558685A (zh) * 2017-06-08 2018-09-21 西安力邦制药有限公司 2,6-二取代苯酚葡甲胺类衍生物及应用
US11628178B2 (en) 2019-03-26 2023-04-18 Epalex Corporation Fospropofol methods and compositions
WO2021078073A1 (zh) * 2019-10-22 2021-04-29 四川大学华西医院 一类取代苯酚羟基酸酯含n衍生物、制备和用途
US11547714B2 (en) 2020-02-05 2023-01-10 Epalex Corporation Fospropofol salts, methods and compositions
WO2022133687A1 (zh) * 2020-12-21 2022-06-30 加拿大力邦制药有限公司 一种药物偶联物、及其制备方法和用途
US11439653B1 (en) 2021-03-30 2022-09-13 Epalex Corporation Fospropofol formulations
US11478490B1 (en) 2021-03-30 2022-10-25 Epalex Corporation Fospropofol formulations

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Publication number Publication date
US20090005352A1 (en) 2009-01-01
US7645792B2 (en) 2010-01-12
US20060041011A1 (en) 2006-02-23
US7241807B2 (en) 2007-07-10

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