TWI369202B - Enantiomerically resolving acyloxyalkyl thiocarbonates used in synthesizing acyloxyalkyl carbamate prodrugs - Google Patents

Enantiomerically resolving acyloxyalkyl thiocarbonates used in synthesizing acyloxyalkyl carbamate prodrugs

Info

Publication number
TWI369202B
TWI369202B TW098103338A TW98103338A TWI369202B TW I369202 B TWI369202 B TW I369202B TW 098103338 A TW098103338 A TW 098103338A TW 98103338 A TW98103338 A TW 98103338A TW I369202 B TWI369202 B TW I369202B
Authority
TW
Taiwan
Prior art keywords
acyloxyalkyl
enantiomerically
resolving
synthesizing
thiocarbonates
Prior art date
Application number
TW098103338A
Other languages
English (en)
Other versions
TW200950775A (en
Inventor
Mark A Gallop
Fenmei Yao
Maria L Ludwikow
Ge Peng
Stephen P Raillard
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 TW200950775A publication Critical patent/TW200950775A/zh
Application granted granted Critical
Publication of TWI369202B publication Critical patent/TWI369202B/zh

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C07C329/02—Monothiocarbonic acids; Derivatives thereof
    • C07C329/04—Esters of monothiocarbonic acids
    • C07C329/06—Esters of monothiocarbonic acids having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • 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
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms 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 carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P11/00—Preparation of sulfur-containing organic compounds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Wood Science & Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Zoology (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Addiction (AREA)
  • Epidemiology (AREA)
  • Analytical Chemistry (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Endocrinology (AREA)
  • Anesthesiology (AREA)
  • Rheumatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Reproductive Health (AREA)
  • Urology & Nephrology (AREA)
  • Pulmonology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
TW098103338A 2008-01-25 2009-01-23 Enantiomerically resolving acyloxyalkyl thiocarbonates used in synthesizing acyloxyalkyl carbamate prodrugs TWI369202B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US2380808P 2008-01-25 2008-01-25
US2381308P 2008-01-25 2008-01-25
US12185908P 2008-12-11 2008-12-11

Publications (2)

Publication Number Publication Date
TW200950775A TW200950775A (en) 2009-12-16
TWI369202B true TWI369202B (en) 2012-08-01

Family

ID=40636729

Family Applications (2)

Application Number Title Priority Date Filing Date
TW098103335A TWI380812B (zh) 2008-01-25 2009-01-23 （３ｓ）-胺甲基-５-甲基己酸前藥之晶形及使用方法
TW098103338A TWI369202B (en) 2008-01-25 2009-01-23 Enantiomerically resolving acyloxyalkyl thiocarbonates used in synthesizing acyloxyalkyl carbamate prodrugs

Family Applications Before (1)

Application Number Title Priority Date Filing Date
TW098103335A TWI380812B (zh) 2008-01-25 2009-01-23 （３ｓ）-胺甲基-５-甲基己酸前藥之晶形及使用方法

Country Status (7)

Country Link
US (1) US8062870B2 (zh)
EP (1) EP2250143B1 (zh)
JP (2) JP5291123B2 (zh)
CA (2) CA2706575C (zh)
ES (1) ES2601852T3 (zh)
TW (2) TWI380812B (zh)
WO (1) WO2009094569A2 (zh)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5291123B2 (ja) * 2008-01-25 2013-09-18 ゼノポート，インコーポレイティド （３ｓ）−アミノメチル−５−ヘキサン酸プロドラッグの結晶形態及びその使用
WO2010017504A1 (en) * 2008-08-07 2010-02-11 Xenoport, Inc. Methods of synthesizing 1-(acyloxy)-alkyl carbamate prodrugs
US7989641B2 (en) 2008-08-07 2011-08-02 Xenoport, Inc. Methods of synthesizing N-hydroxysuccinimidyl carbonates
AR073361A1 (es) * 2008-09-05 2010-11-03 Gruenenthal Gmbh Combinacion farmaceutica que comprende 3-(-3-dimetilamino-1-etil-2-metil-propil)-fenol y un antiepileptico. uso
JP2012519212A (ja) 2009-03-03 2012-08-23 ゼノポート，インコーポレイティド Ｒ−バクロフェンプロドラッグの持効性放出経口投与形
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
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
EP2961730A2 (en) 2013-02-26 2016-01-06 XenoPort, Inc. Method of making 1-(acyloxy)-alkyl carbamate compounds
TR201909632T4 (tr) 2013-11-05 2019-07-22 Astrazeneca Ab Nmda antagonisti ön ilaçları.
JPWO2019069872A1 (ja) 2017-10-04 2020-09-10 日本化薬株式会社 紫外線硬化型接着剤組成物、その硬化物および紫外線硬化型接着剤組成物を用いた光学部材の製造方法
WO2024109817A1 (en) * 2022-11-24 2024-05-30 Xgene Pharmaceutical Inc. Naproxen and pregabalin 1- (acyloxy) -alkyl carbamate drug conjugate purification process

Family Cites Families (65)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2460891C2 (de) 1974-12-21 1982-09-23 Gödecke AG, 1000 Berlin 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
US4126684A (en) 1976-02-11 1978-11-21 Ciba-Geigy Corporation 4-amino-3-p-halophenylbutyric acids and their derivatives used in the control of narcotic abuse
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
US5006560A (en) 1989-12-20 1991-04-09 Schering Corporation Use of GABA-B selective agonists as anti-tussive agents
US6197819B1 (en) 1990-11-27 2001-03-06 Northwestern University Gamma amino butyric acid analogs and optical isomers
WO1992009560A1 (en) 1990-11-27 1992-06-11 Northwestern University Gaba and l-glutamic acid analogs for antiseizure treatment
SK283281B6 (sk) 1992-05-20 2003-05-02 Northwestern University Deriváty gamaaminomaslovej kyseliny, spôsoby a medziprodukty na ich výrobu, ich použitie a farmaceutické prostriedky
GB9308430D0 (en) 1993-04-23 1993-06-09 Glaxo Group Ltd Medicaments
US5684018A (en) 1994-12-13 1997-11-04 Merck & Co., Inc. Acyloxyisopropyl carbamates as prodrugs for amine drugs
PT888325E (pt) 1996-02-07 2002-10-31 Warner Lambert Co Novos amino acidos ciclicos como agentes farmaceuiticos
CA2244912C (en) 1996-03-14 2005-07-12 Warner-Lambert Company Novel substituted cyclic amino acids as pharmaceutical agents
EA001214B1 (ru) 1996-03-14 2000-12-25 Варнер-Ламберт Компани Новые мостиковые циклические аминокислоты как фармацевтически применимые вещества
SE9603408D0 (sv) 1996-09-18 1996-09-18 Astra Ab Medical use
US6153650A (en) 1996-10-23 2000-11-28 Warner-Lambert Company Substituted gamma aminobutyric acids as pharmaceutical agents
AU8668598A (en) 1997-08-20 1999-03-08 University Of Oklahoma, The Gaba analogs to prevent and treat gastrointestinal damage
CN1138755C (zh) 1997-10-27 2004-02-18 沃尼尔·朗伯公司 作为药物的环状氨基酸及其衍生物
KR20010033154A (ko) 1997-12-16 2001-04-25 로즈 암스트롱, 크리스틴 에이. 트러트웨인 제약물로서의 신규한 아민
CN1495160A (zh) 1997-12-16 2004-05-12 ��ʲ 1-取代-1-氨基甲基-环烷衍生物（＝加巴喷丁类似物）、其制备及其在治疗神经病方面的用途
IL135315A0 (en) 1997-12-16 2001-05-20 Warner Lambert Co 4(3)-substituted-4(3)-aminomethyl-(thio)pyran or -piperidine derivatives (gabapentin analogues), their preparation and their use in the treatment of neurological disorders
CA2322558C (en) 1998-05-26 2006-04-11 Warner-Lambert Company Conformationally constrained amino acid compounds having affinity for the alpha2delta subunit of a calcium channel
AU5478799A (en) 1998-09-14 2000-04-03 Warner-Lambert Company Branched alkyl pyrrolidine-3-carboxylic acids
US6627771B1 (en) 1998-11-25 2003-09-30 Pfizer Inc Gamma amino butyric and acid analogs
EP1031350A1 (en) 1999-02-23 2000-08-30 Warner-Lambert Company Use of a gabapentin-analog for the manufacture of a medicament for preventing and treating visceral pain
IL145763A0 (en) 1999-04-08 2002-07-25 Warner Lambert Co Method for the treatment of incontinence
IT1313585B1 (it) 1999-07-30 2002-09-09 Neuroscienze S C A R L Uso di agonisti dei recettori gabab per la terapia di mantenimentodell'astinenza da nicotina in soggetti nicotino-dipendenti.
JP2003506065A (ja) * 1999-08-05 2003-02-18 ノボ ノルディスク アクティーゼルスカブ 置換された３−フェニル−プロパン酸エステル及び置換された３−フェニル−プロパン酸の調製の方法
SK286621B6 (sk) 1999-08-20 2009-02-05 Ortho-Mcneil Pharmaceutical, Inc. Farmaceutický prostriedok obsahujúci kombináciu tramadolového materiálu a antikonvulzívneho činidla, táto kombinácia a jej použitie na výrobu liečiva
IT1319275B1 (it) 1999-10-08 2003-09-26 Neuroscienze S C A R L Uso del baclofen nel trattamento dell'astinenza da etanolo.
IL152770A0 (en) 2000-06-26 2003-06-24 Warner Lambert Co Gabapentin analogues for sleep disorders
GB2374595A (en) 2001-04-19 2002-10-23 Warner Lambert Co Fused bicyclic or tricyclic amino acids
KR20040020056A (ko) 2001-05-29 2004-03-06 디포메드 디벨롭먼트 리미티드 위식도 역류 질환 및 야간 위산분비의 치료 방법
US8048917B2 (en) * 2005-04-06 2011-11-01 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US7232924B2 (en) 2001-06-11 2007-06-19 Xenoport, Inc. Methods for synthesis of acyloxyalkyl derivatives of GABA analogs
US6818787B2 (en) * 2001-06-11 2004-11-16 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
ES2380287T3 (es) * 2001-06-11 2012-05-10 Xenoport, Inc. Profármacos de análogos de GABA, composiciones y sus usos
US7186855B2 (en) 2001-06-11 2007-03-06 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
EP1485082A4 (en) * 2002-02-19 2009-12-30 Xenoport Inc PROCESS FOR THE SYNTHESIS OF PROMEDICAMENTS FROM 1-ACYL-ALKYL DERIVATIVES AND CORRESPONDING COMPOSITIONS
WO2003080588A1 (en) 2002-03-20 2003-10-02 Xenoport Cyclic 1-(acyloxy)-alkyl prodrugs of gaba analogs, compositions and uses thereof
PE20040991A1 (es) * 2002-08-12 2004-12-27 Lundbeck & Co As H Separacion de intermediarios para la preparacion de escitalopram
KR100845932B1 (ko) * 2002-12-13 2008-07-11 워너-램버트 캄파니 엘엘씨 섬유근육통 및 기타 관련 질환의 치료를 위한 프레가발린및 그의 유도체
CA2451267A1 (en) 2002-12-13 2004-06-13 Warner-Lambert Company Llc Pharmaceutical uses for alpha2delta ligands
KR20050119676A (ko) 2003-03-31 2005-12-21 제노포트 인코포레이티드 가바 유사체의 프로드러그를 사용한 열성 홍조의 치료 또는예방
US7662987B2 (en) 2003-07-15 2010-02-16 Xenoport, Inc. Methods for synthesis of acyloxyalkyl compounds
EP1660440B1 (en) * 2003-08-20 2012-02-22 XenoPort, Inc. Acyloxyalkyl carbamate prodrugs, methods of synthesis and use
WO2005019163A2 (en) 2003-08-20 2005-03-03 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs, methods of synthesis and use
US7700652B2 (en) 2003-09-11 2010-04-20 Xenoport, Inc. Treating urinary incontinence using prodrugs of GABA analogs
EP1675582A1 (en) 2003-09-12 2006-07-05 Warner-Lambert Company LLC Combination comprising an alpha-2-delta ligand and an ssri and/or snri for treatment of depression and anxiety disorders
SG146643A1 (en) 2003-09-17 2008-10-30 Xenoport Inc Treating or preventing restless legs syndrome using prodrugs of gaba analogs
JP2007506729A (ja) 2003-09-25 2007-03-22 ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー α２δタンパク質に親和性を有するアミノ酸のプロドラッグ
EP2371815A1 (en) * 2003-12-30 2011-10-05 XenoPort, Inc. Sythesis of acyloxyalkyl carbamate prodrugs and intermediates thereof
US20050209319A1 (en) * 2004-03-18 2005-09-22 Xenoport, Inc. Treatment of local pain
NZ533360A (en) * 2004-06-04 2007-02-23 Ind Res Ltd Improved method for preparing 3-hydroxy-4-hydroxymethyl-pyrrolidine compounds
JP2006050990A (ja) * 2004-08-13 2006-02-23 Kaneka Corp 光学活性２−置換−３−（４−置換オキシフェニル）プロピオン酸およびその対掌体エステルの製造方法
DE102004040736B4 (de) * 2004-08-23 2007-01-11 Sanofi-Aventis Deutschland Gmbh Verfahren zur Herstellung von Diarylcycloalkylderivaten
WO2006108151A1 (en) * 2005-04-06 2006-10-12 Teva Pharmaceutical Industries Ltd. Crystalline forms of pregabalin
DE102005028492A1 (de) * 2005-06-20 2006-12-28 Basf Ag Verfahren zur Herstellung von optisch aktiven Aminoalkylphenolen
WO2007027477A2 (en) 2005-08-23 2007-03-08 Xenoport, Inc. Treating vulvodynia using prodrugs of gaba analogs
WO2007027476A2 (en) 2005-08-26 2007-03-08 Xenoport, Inc. Treating premature ejaculation using gabapentin and pregabalin prodrugs
MXPA05011735A (es) 2005-11-01 2007-04-30 Leopoldo Espinosa Abdala Composiciones farmaceuticas que comprenden combinaciones de analgesicos y anticonvulsivantes para el tratamiento del dolor agudo y cronico.
TW200800155A (en) * 2005-12-29 2008-01-01 Depomed Inc Gastric retentive gabapentin dosage forms and methods for using same
JP2010512314A (ja) 2006-12-08 2010-04-22 ゼノポート，インコーポレーテッド 疾患を治療するためのｇａｂａアナログのプロドラッグの使用
WO2009061934A1 (en) * 2007-11-06 2009-05-14 Xenoport, Inc. Use of prodrugs of gaba b agonists for treating neuropathic and musculoskeletal pain
JP5291123B2 (ja) * 2008-01-25 2013-09-18 ゼノポート，インコーポレイティド （３ｓ）−アミノメチル−５−ヘキサン酸プロドラッグの結晶形態及びその使用
WO2009094577A2 (en) * 2008-01-25 2009-07-30 Xenoport, Inc. Mesophasic forms of (3s)-aminomethyl-5-methyl-hexanoic acid prodrugs and methods of use

Also Published As

Publication number Publication date
CA2706575C (en) 2015-07-14
WO2009094569A3 (en) 2009-10-08
JP2011509692A (ja) 2011-03-31
TWI380812B (zh) 2013-01-01
TW200950775A (en) 2009-12-16
CA2710538A1 (en) 2009-07-30
CA2706575A1 (en) 2009-07-30
JP2011510930A (ja) 2011-04-07
TW200944198A (en) 2009-11-01
WO2009094569A2 (en) 2009-07-30
ES2601852T3 (es) 2017-02-16
US8062870B2 (en) 2011-11-22
JP5291123B2 (ja) 2013-09-18
EP2250143B1 (en) 2016-04-20
JP5563483B2 (ja) 2014-07-30
EP2250143A2 (en) 2010-11-17
US20090192325A1 (en) 2009-07-30

Similar Documents

Publication Publication Date Title
TWI369202B (en) Enantiomerically resolving acyloxyalkyl thiocarbonates used in synthesizing acyloxyalkyl carbamate prodrugs
FR19C1012I2 (fr) Composes de tetracycline c7-fluorosubstituee
HRP20140223T1 (en) Dolutegravir prodrugs
GB2471241B (en) Dynamic advertisement stream replacement
EP2370026A4 (en) SPINAL CAGE WITH LOCKABLE EXPANSION
EP2393472A4 (en) AMPHIPHILIC PRODRUGS
EP2376521A4 (en) INSULIN-BASED AMIDE-BASED PRODRUGS
HK1162199A1 (zh) 異質 方法
DK2349217T3 (da) Gamma-hydroxysmørsyre-granulat
IL209382A0 (en) Water-soluble acetaminophen analogs
HK1157339A1 (zh) 增添對映體的芳基唑基- 氰乙氨基殺寄生蟲的化合物
EP2423215A4 (en) COMMITICAL-BASED PRODRUGS AND SYNTHETIC METHOD AND APPLICATION
IL209384A0 (en) Hepatoprotectant acetaminophen mutual prodrugs
BR112012005598A2 (pt) profármacos de guanfacina
IL208280A0 (en) Hydroxymethylcylohexyl amines
EP2274061A4 (en) ELECTROSTATIC TOY
IL213031A0 (en) Thiadiazole-substituted arylamides
EP2118052A4 (en) NEW PRODRUGS
HK1183298A1 (zh) 對映異構體純的胺
EP2269485A4 (en) POLYACETAL-CONTAINING BRUSH
ITVA20070023A1 (it) Esteri idrossammici come fotoiniziatori
HK1162019A1 (en) Indanyl compounds
GB2460330B (en) Signage
HU3724U (en) Billboard using moire effect
HU0900055V0 (en) Billboard using moire effect

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees