CA2551859C - Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof - Google Patents

Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof Download PDF

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Publication number
CA2551859C
CA2551859C CA2551859A CA2551859A CA2551859C CA 2551859 C CA2551859 C CA 2551859C CA 2551859 A CA2551859 A CA 2551859A CA 2551859 A CA2551859 A CA 2551859A CA 2551859 C CA2551859 C CA 2551859C
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Canada
Prior art keywords
substituted
formula
compound
carbon
attached
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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 - Lifetime
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CA2551859A
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English (en)
French (fr)
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CA2551859A1 (en
Inventor
Mark A. Gallop
Xuedong Dai
Randall A. Scheuerman
Stephen P. Raillard
Suresh K. Manthati
Fenmei Yao
Thu Phan
Maria Ludwikow
Ge Peng
Seema Bhat
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Arbor Pharmaceuticals LLC
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XenoPort Inc
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Publication date
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Publication of CA2551859A1 publication Critical patent/CA2551859A1/en
Application granted granted Critical
Publication of CA2551859C publication Critical patent/CA2551859C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—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 two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • 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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—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 two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2551859A 2003-12-30 2004-12-30 Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof Expired - Lifetime CA2551859C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US53364903P 2003-12-30 2003-12-30
US60/533,649 2003-12-30
US60663704P 2004-08-13 2004-08-13
US60/606,637 2004-08-13
PCT/US2004/043823 WO2005066122A2 (en) 2003-12-30 2004-12-30 Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof

Publications (2)

Publication Number Publication Date
CA2551859A1 CA2551859A1 (en) 2005-07-21
CA2551859C true CA2551859C (en) 2011-10-04

Family

ID=34753006

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2551859A Expired - Lifetime CA2551859C (en) 2003-12-30 2004-12-30 Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof

Country Status (9)

Country Link
US (5) US7227028B2 (https=)
EP (2) EP1716115B1 (https=)
JP (2) JP4927563B2 (https=)
CN (1) CN102702065A (https=)
CA (1) CA2551859C (https=)
DK (1) DK1716115T3 (https=)
ES (1) ES2405329T3 (https=)
IL (2) IL176341A (https=)
WO (1) WO2005066122A2 (https=)

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US8299291B2 (en) * 2008-08-07 2012-10-30 Xenoport, Inc. Methods of synthesizing 1-(acyloxy)-alkyl carbamate prodrugs
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KR101937782B1 (ko) 2011-03-01 2019-01-11 파넥스트 바클로펜 및 아캄프로세이트에 기초한 신경 장애의 치료
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Also Published As

Publication number Publication date
US20070037988A9 (en) 2007-02-15
CA2551859A1 (en) 2005-07-21
JP2007518723A (ja) 2007-07-12
US8003809B2 (en) 2011-08-23
WO2005066122A3 (en) 2005-10-13
ES2405329T3 (es) 2013-05-30
JP5670842B2 (ja) 2015-02-18
IL200821A (en) 2013-03-24
JP4927563B2 (ja) 2012-05-09
US20120010425A1 (en) 2012-01-12
DK1716115T3 (da) 2013-05-27
US20050222431A1 (en) 2005-10-06
EP1716115B1 (en) 2013-02-27
US20130131355A1 (en) 2013-05-23
CN102702065A (zh) 2012-10-03
US9353057B2 (en) 2016-05-31
US8378137B2 (en) 2013-02-19
US20090216037A1 (en) 2009-08-27
US7511158B2 (en) 2009-03-31
US20070244331A1 (en) 2007-10-18
EP1716115A2 (en) 2006-11-02
JP2011236247A (ja) 2011-11-24
WO2005066122A2 (en) 2005-07-21
IL176341A0 (en) 2008-02-09
IL176341A (en) 2013-03-24
EP2371815A1 (en) 2011-10-05
HK1090924A1 (en) 2007-01-05
US7227028B2 (en) 2007-06-05

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