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
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 - 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
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arbor Pharmaceuticals LLC
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XenoPort Inc
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Publication date
Application filed by XenoPort Inc filed Critical XenoPort Inc
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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Classifications

    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (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 (enExample)
EP (2) EP2371815A1 (enExample)
JP (2) JP4927563B2 (enExample)
CN (1) CN102702065A (enExample)
CA (1) CA2551859C (enExample)
DK (1) DK1716115T3 (enExample)
ES (1) ES2405329T3 (enExample)
IL (2) IL176341A (enExample)
WO (1) WO2005066122A2 (enExample)

Families Citing this family (63)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7186855B2 (en) 2001-06-11 2007-03-06 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US8048917B2 (en) * 2005-04-06 2011-11-01 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US7025745B2 (en) * 2002-10-07 2006-04-11 Advanced Cardiovascular Systems, Inc. Method of making a catheter balloon using a tapered mandrel
WO2005010011A2 (en) * 2003-07-15 2005-02-03 Xenoport, Inc. Methods of synthesis of acyloxyalkyl compounds
AU2004267100B2 (en) * 2003-08-20 2010-10-07 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs, methods of synthesis and use
CA2537837A1 (en) * 2003-09-11 2005-03-24 Xenoport, Inc. Treating and/or preventing urinary incontinence using prodrugs of gaba analogs
CA2541752C (en) * 2003-10-14 2012-01-03 Xenoport, Inc. Crystalline form of gamma-aminobutyric acid analog
CA2551859C (en) 2003-12-30 2011-10-04 Xenoport, Inc. Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof
EP1809619A1 (en) * 2004-10-21 2007-07-25 Transtech Pharma, Inc. Bissulfonamide compounds as agonists of galr1, compositions, and methods of use
US7494985B2 (en) 2004-11-03 2009-02-24 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs, methods of synthesis, and use
EP1811986B1 (en) 2004-11-04 2014-03-26 XenoPort, Inc. Gabapentin prodrug sustained release oral dosage forms
EP1919859B1 (en) * 2005-06-20 2010-06-02 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs of tranexamic acid and use
WO2007085933A2 (en) * 2006-01-25 2007-08-02 Glenmark Pharmaceuticals Limited Process for the preparation of n-[1-(s)-ethoxycarbonyl-1-butyl]-(s)-alanine-dmt complex and its use in the preparation of perindopril
TW200820963A (en) 2006-07-28 2008-05-16 Xenoport Inc Acyloxyalkyl carbamate prodrugs of α-amino acids, methods of synthesis and use
WO2008033572A1 (en) 2006-09-15 2008-03-20 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs, methods of synthesis and use
CA2674610C (en) * 2007-01-11 2013-06-18 Xenoport, Inc. Sustained release oral dosage forms of a prodrug of r-baclofen and methods of treatment
US20090118365A1 (en) * 2007-11-06 2009-05-07 Xenoport, Inc Use of Prodrugs of GABA B Agonists for Treating Neuropathic and Musculoskeletal Pain
WO2009094563A2 (en) 2008-01-25 2009-07-30 Xenoport, Inc. Crystalline form of calcium-salts of (3s)-aminomethyl-b-methyl-hexanoic acids and methods of use
WO2009094577A2 (en) * 2008-01-25 2009-07-30 Xenoport, Inc. Mesophasic forms of (3s)-aminomethyl-5-methyl-hexanoic acid prodrugs and methods of use
CA2710538A1 (en) * 2008-01-25 2009-07-30 Xenoport, Inc. Crystalline form of a (3s)-aminomethyl-5-methyl-hexanoic acid prodrug and methods of use
WO2009096985A1 (en) * 2008-02-01 2009-08-06 Xenoport, Inc. Sustained release particulate oral dosage forms of (r)-baclofen prodrugs and methods of treatment
US20100137442A2 (en) * 2008-02-01 2010-06-03 Xenoport, Inc. Sustained Release Particulate Oral Dosage Forms of (R)-Baclofen and Methods of Treatment
SG157299A1 (en) 2008-05-09 2009-12-29 Agency Science Tech & Res Diagnosis and treatment of kawasaki disease
WO2010008886A2 (en) * 2008-06-24 2010-01-21 Teva Pharmaceutical Industries Ltd. Processes for preparing prodrugs of gabapentin and intermediates thereof
KR20110028320A (ko) * 2008-07-02 2011-03-17 테바 파마슈티컬 인더스트리즈 리미티드 가바펜틴 에나카르빌 염 및 이의 제조 방법
WO2010017498A1 (en) * 2008-08-07 2010-02-11 Xenoport, Inc. Methods of synthesizing n-hydroxysuccinimidyl carbonates
WO2010017504A1 (en) * 2008-08-07 2010-02-11 Xenoport, Inc. Methods of synthesizing 1-(acyloxy)-alkyl carbamate prodrugs
WO2010063002A2 (en) * 2008-11-26 2010-06-03 Teva Pharmaceutical Industries Ltd. Processes for the preparation and purification of gabapentin enacarbil
WO2010075520A1 (en) 2008-12-23 2010-07-01 Teva Pharmaceutical Industries Ltd. Preparation of gabapentin enacarbil intermediate
US10071068B2 (en) * 2009-03-03 2018-09-11 Xenoport, Inc. Sustained release oral dosage forms of an R-baclofen prodrug
CN102341098A (zh) * 2009-03-06 2012-02-01 什诺波特有限公司 具有高负荷的加巴喷丁前药的口服剂型
EP2419401A2 (en) * 2009-04-17 2012-02-22 XenoPort, Inc. GAMMA-AMINO-BUTYRIC ACID DERIVATIVES AS GABAb RECEPTOR LIGANDS
WO2011012723A1 (en) 2009-07-31 2011-02-03 Ascendis Pharma As Injectable sustained release compositions comprising a pramipexole prodrug
US20120191039A1 (en) 2009-07-31 2012-07-26 Ascendis Pharma A/S Carrier linked pramipexole prodrugs
WO2011028234A1 (en) * 2009-09-04 2011-03-10 Xenoport, Inc. Uses of acyloxyalkyl carbamate prodrugs of tranexamic acid
US20110130454A1 (en) * 2009-11-24 2011-06-02 Xenoport, Inc. Prodrugs of gamma-amino acid, alpha-2-delta ligands, pharmaceutical compositions and uses thereof
US20110124705A1 (en) * 2009-11-24 2011-05-26 Xenoport, Inc. Prodrugs of alpha-2-delta ligands, pharmaceutical compositions and uses thereof
WO2011091164A1 (en) 2010-01-22 2011-07-28 Xenoport, Inc. Oral dosage forms having a high loading of a tranexamic acid prodrug
WO2011109403A1 (en) 2010-03-01 2011-09-09 Xenoport, Inc. Use of (3r)-4-{[(1s)-2-methyl-1- (2-methylpropanoyloxy)propoxy]carbonylamino}-3-(4-chlorophenyl) butanoic acid for treating urinary incontinence
EP2937334B1 (en) * 2010-03-10 2017-04-19 Promentis Pharmaceuticals, Inc. Propionic acids, propionic acid esters, and related compounds
SG10201502026XA (en) 2010-03-18 2015-05-28 Daiichi Sankyo Co Ltd Cycloalkyl-substituted imidazole derivative
US9248111B2 (en) 2011-03-01 2016-02-02 Pharnext Therapeutic approaches for treating parkinson's disease
EP2705842A1 (en) 2012-09-05 2014-03-12 Pharnext Therapeutic approaches for treating parkinson's disease
RS53227B (sr) 2011-03-01 2014-08-29 Pharnext Terapija neuroloških poremećaja kombinacijom baklofena i akamprosata
UA115968C2 (uk) 2011-03-01 2018-01-25 Фарнекст Нові композиції для лікування неврологічних захворювань
US8580850B2 (en) 2011-08-11 2013-11-12 Xenoport, Inc. Anhydrous and hemihydrate crystalline forms of an (R)-baclofen prodrug, methods of synthesis and methods of use
WO2013026777A1 (en) * 2011-08-24 2013-02-28 Solvay Sa Fluoroalkyl s-(fluoro)alkyl thiocarbonates, a method for the preparation of fluoroalkyl s-(fluoro)alkyl thiocarbonates, and their use
SG11201500309VA (en) 2012-07-18 2015-02-27 Pharnext Baclofen and acamprosate based therapy of macular degeneration disorders
EP2705843A1 (en) 2012-09-05 2014-03-12 Pharnext Therapeutic approaches for treating epilepsy and related disorders through reduction of epileptogenesis
EP2705841A1 (en) 2012-09-05 2014-03-12 Pharnext Combinations of nootropic agents for treating cognitive dysfunctions
EP2961730A2 (en) 2013-02-26 2016-01-06 XenoPort, Inc. Method of making 1-(acyloxy)-alkyl carbamate compounds
KR102336426B1 (ko) 2013-11-05 2021-12-08 아스트라제네카 아베 Nmda 길항제 전구약물
EP3102195B1 (en) 2014-02-03 2021-10-06 Quadriga Biosciences, Inc. Beta-substituted beta-amino acids and analogs as chemotherapeutic agents
EP3102194A1 (en) 2014-02-03 2016-12-14 Quadriga Biosciences, Inc. Beta-substituted gamma-amino acids and analogs as chemotherapeutic agents
EP3104850A1 (en) 2014-02-11 2016-12-21 Pharnext Combination of baclofen, acamprosate and medium chain triglycerides for the treatment of neurological disorders
ES3072651T3 (en) 2014-10-17 2026-07-03 Univ Illinois Scalable synthesis of reduced toxicity derivative of amphotericin b
JPWO2016208709A1 (ja) 2015-06-26 2018-04-19 第一三共株式会社 １−（アシルオキシ）アルキルカルバメート誘導体の新規な製造方法
AR105592A1 (es) 2015-08-03 2017-10-18 Quadriga Biosciences Inc b-AMINOÁCIDOS b-SUSTITUIDOS Y ANÁLOGOS COMO AGENTES QUIMIOTERAPÉUTICOS Y USOS DE LOS MISMOS
EP3339291A1 (en) 2016-12-22 2018-06-27 Vita Api Proteasome inhibiting ss-lactam prodrugs useful for the treatment of cancer and neurodegenerative disorders
US10736876B2 (en) 2017-04-24 2020-08-11 Pharnext Idalopirdine-based combinatorial therapies of Alzheimer's disease
CN108976147B (zh) * 2017-05-31 2021-02-12 首都医科大学 氨基正己酰氨基甲环酰氨基正己酰碱性氨基酸，其合成，活性和应用
CN111902138A (zh) 2018-01-29 2020-11-06 法奈克斯公司 在乙酰胆碱酯酶抑制剂治疗失去反应的患者中对阿兹海默氏病的基于巴氯芬和阿坎酸的治疗
IL309210A (en) * 2021-06-09 2024-02-01 Atai Therapeutics Inc Parent drugs and conjugates of dimethyltryptamine

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0079872B1 (en) 1981-11-17 1985-03-20 KabiVitrum AB Antifibrinolytically active compounds
US4426391A (en) 1982-09-15 1984-01-17 Merck & Co., Inc. [(Alkoxycarbonyl)oxy]alkyl esters of methyldopa
US4760057A (en) 1983-06-23 1988-07-26 Merck & Co., Inc. (Acyloxyalkoxy)carbonyl derivatives as bioreversible prodrug moieties for primary and secondary amine functions in drugs
US4916230A (en) * 1984-07-02 1990-04-10 Merck & Co., Inc. Process for preparing novel N-(acyloxy-alkoxy)carbonyl derivatives useful as bioreversible prodrug moieties for primary and secondary amine functions in drugs
JP2629375B2 (ja) * 1989-09-14 1997-07-09 日立化成工業株式会社 アミノ基が保護されたドーパ又はドーパ誘導体の製造法
US5098999A (en) 1989-08-23 1992-03-24 Hitachi Chemical Company Amino-protected dopa derivative and production thereof
DE69023844T2 (de) 1989-09-06 1996-06-20 Merck & Co Inc Acyloxymethylester der Bisphonsäuren als Knochenresorptions-Inhibitoren.
GB9001405D0 (en) * 1990-01-22 1990-03-21 Leo Pharm Prod Ltd New intermediates,their production and use
SE9200858L (sv) * 1992-03-20 1993-09-21 Kabi Pharmacia Ab Metod för framställning av pellets med fördröjd frisättning
SE9300013L (sv) 1992-12-30 1994-07-01 Kabi Pharmacia Ab Nytt förfarande och mellanprodukter för framställning av pro- läkemedel
IL111584A0 (en) * 1993-11-18 1995-01-24 Merck & Co Inc Prodrugs of an inhibitor of hiv protease and pharmaceutical compositions containing them
US5684018A (en) * 1994-12-13 1997-11-04 Merck & Co., Inc. Acyloxyisopropyl carbamates as prodrugs for amine drugs
JPH10148903A (ja) * 1996-11-20 1998-06-02 Konica Corp 耐圧性の改良されたハロゲン化銀写真感光材料
JP3526243B2 (ja) 1999-07-09 2004-05-10 松下電器産業株式会社 基地局装置及び回線品質劣化防止方法
JP2003505396A (ja) * 1999-07-15 2003-02-12 イーライ・リリー・アンド・カンパニー プソイドマイシンプロドラッグ
GB2365425A (en) * 2000-08-01 2002-02-20 Parke Davis & Co Ltd Alkyl amino acid derivatives useful as pharmaceutical agents
AU2002310409C1 (en) * 2001-06-11 2008-04-17 Xenoport, Inc. Orally administered dosage forms of GABA analog prodrugs having reduced toxicity
AU2004267100B2 (en) * 2003-08-20 2010-10-07 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs, methods of synthesis and use
US7265140B2 (en) * 2003-09-23 2007-09-04 Pfizer Inc Acyloxymethylcarbamate prodrugs of oxazolidinones
CA2551859C (en) 2003-12-30 2011-10-04 Xenoport, Inc. Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof
US7494985B2 (en) 2004-11-03 2009-02-24 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs, methods of synthesis, and use
US7566738B2 (en) 2004-11-03 2009-07-28 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs of sulfinic acids, methods of synthesis, and use

Also Published As

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

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