JP4216713B2 - Ｇａｂａ類似体のプロドラッグ、組成物およびその使用 - Google Patents

Ｇａｂａ類似体のプロドラッグ、組成物およびその使用 Download PDF

Info

Publication number
JP4216713B2
JP4216713B2 JP2003516067A JP2003516067A JP4216713B2 JP 4216713 B2 JP4216713 B2 JP 4216713B2 JP 2003516067 A JP2003516067 A JP 2003516067A JP 2003516067 A JP2003516067 A JP 2003516067A JP 4216713 B2 JP4216713 B2 JP 4216713B2
Authority
JP
Japan
Prior art keywords
substituted
compounds
benzyl
acid
butyl
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
Application number
JP2003516067A
Other languages
English (en)
Japanese (ja)
Other versions
JP2004536873A (ja
JP2004536873A5 (enExample
Inventor
エー． ギャロップ，マーク
シー． カンディー，ケネス
エックス． ツォウ，シンディ
ジー． キウ，フェヤン
ヤオ，フェンメイ
シアン，ジア−ニン
アール． オルマン，イアン
Original Assignee
ゼノポート，インコーポレイティド
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27404495&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JP4216713(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by ゼノポート，インコーポレイティド filed Critical ゼノポート，インコーポレイティド
Publication of JP2004536873A publication Critical patent/JP2004536873A/ja
Publication of JP2004536873A5 publication Critical patent/JP2004536873A5/ja
Application granted granted Critical
Publication of JP4216713B2 publication Critical patent/JP4216713B2/ja
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C07C229/06—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 having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—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 having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/12—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 having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/555—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound pre-targeting systems involving an organic compound, other than a peptide, protein or antibody, for targeting specific cells
    • 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/24—Antidepressants
    • 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
    • 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
    • A61P39/00—General protective or antinoxious agents
    • A61P39/02—Antidotes
    • 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
    • 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
    • C07C323/57—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 the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—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 the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D267/02—Seven-membered rings
    • C07D267/06—Seven-membered rings having the hetero atoms in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
    • C07D307/58—One oxygen atom, e.g. butenolide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings 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
    • C07D317/34—Oxygen atoms
    • C07D317/40—Vinylene carbonate; Substituted vinylene carbonates
    • 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

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Emergency Medicine (AREA)
  • Immunology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Molecular Biology (AREA)
  • Addiction (AREA)
  • Rheumatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Oncology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Psychology (AREA)
  • Anesthesiology (AREA)
  • Communicable Diseases (AREA)
  • Toxicology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
JP2003516067A 2001-06-11 2002-06-11 Ｇａｂａ類似体のプロドラッグ、組成物およびその使用 Expired - Lifetime JP4216713B2 (ja)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US29752101P 2001-06-11 2001-06-11
US29851401P 2001-06-14 2001-06-14
US36609002P 2002-03-19 2002-03-19
PCT/US2002/018689 WO2002100347A2 (en) 2001-06-11 2002-06-11 Prodrugs of gaba analogs, compositions and uses thereof

Related Child Applications (2)

Application Number Title Priority Date Filing Date
JP2008171250A Division JP2009051822A (ja) 2001-06-11 2008-06-30 Ｇａｂａ類似体のプロドラッグ、組成物およびその使用
JP2008171589A Division JP5001227B2 (ja) 2001-06-11 2008-06-30 Ｇａｂａ類似体のプロドラッグ、組成物およびその使用

Publications (3)

Publication Number Publication Date
JP2004536873A JP2004536873A (ja) 2004-12-09
JP2004536873A5 JP2004536873A5 (enExample) 2005-12-15
JP4216713B2 true JP4216713B2 (ja) 2009-01-28

Family

ID=27404495

Family Applications (4)

Application Number Title Priority Date Filing Date
JP2003516067A Expired - Lifetime JP4216713B2 (ja) 2001-06-11 2002-06-11 Ｇａｂａ類似体のプロドラッグ、組成物およびその使用
JP2003503214A Pending JP2004534057A (ja) 2001-06-11 2002-06-11 低毒性を示す経口投与剤形のｇａｂａ類似体プロドラッグ
JP2008171250A Withdrawn JP2009051822A (ja) 2001-06-11 2008-06-30 Ｇａｂａ類似体のプロドラッグ、組成物およびその使用
JP2008171589A Expired - Lifetime JP5001227B2 (ja) 2001-06-11 2008-06-30 Ｇａｂａ類似体のプロドラッグ、組成物およびその使用

Family Applications After (3)

Application Number Title Priority Date Filing Date
JP2003503214A Pending JP2004534057A (ja) 2001-06-11 2002-06-11 低毒性を示す経口投与剤形のｇａｂａ類似体プロドラッグ
JP2008171250A Withdrawn JP2009051822A (ja) 2001-06-11 2008-06-30 Ｇａｂａ類似体のプロドラッグ、組成物およびその使用
JP2008171589A Expired - Lifetime JP5001227B2 (ja) 2001-06-11 2008-06-30 Ｇａｂａ類似体のプロドラッグ、組成物およびその使用

Country Status (20)

Country Link
US (2) US6833140B2 (enExample)
EP (4) EP1404310A4 (enExample)
JP (4) JP4216713B2 (enExample)
KR (5) KR20090121404A (enExample)
CN (1) CN1533270A (enExample)
AT (2) ATE540678T1 (enExample)
AU (4) AU2002345664C1 (enExample)
CA (2) CA2449729C (enExample)
CY (1) CY1107894T1 (enExample)
DE (1) DE60223923T3 (enExample)
DK (1) DK1404324T4 (enExample)
ES (2) ES2296956T5 (enExample)
HU (2) HUP0400167A3 (enExample)
IL (5) IL159299A0 (enExample)
MX (2) MXPA03011566A (enExample)
NO (4) NO20035473D0 (enExample)
NZ (1) NZ567711A (enExample)
PT (1) PT1404324E (enExample)
WO (2) WO2002100347A2 (enExample)
ZA (1) ZA200309679B (enExample)

Families Citing this family (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL139298A0 (en) * 1998-05-15 2001-11-25 Warner Lambert Co Stabilized pharmaceutical preparations of gamma-aminobutyric acid derivatives and process for preparing the same
AU2002243204A1 (en) 2000-10-06 2002-06-11 Xenoport, Inc. Bile-acid derived compounds for enhancing oral absorption and systemic bioavailability of drugs
AU2002211863A1 (en) * 2000-10-06 2002-04-15 Xenoport, Inc. Bile-acid derived compounds for providing sustained systemic concentrations of drugs after oral administration
AU2002211538A1 (en) * 2000-10-06 2002-04-15 Xenoport, Inc. Compounds for sustained release of orally delivered drugs
EP1361847A2 (en) 2000-10-06 2003-11-19 Xenoport, Inc. Bile-acid conjugates for providing sustained systemic concentrations of drugs
US8048917B2 (en) 2005-04-06 2011-11-01 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US7186855B2 (en) 2001-06-11 2007-03-06 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US6818787B2 (en) * 2001-06-11 2004-11-16 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US7420002B2 (en) * 2001-06-11 2008-09-02 Xenoport Amino acid conjugates providing for sustained systemic concentrations of GABA analogues
MXPA03011566A (es) * 2001-06-11 2004-10-28 Xenoport Inc Formas de dosificacion de profarmacos de analogos de gaba administrados oralmente que tienen toxicidad reducida.
US7232924B2 (en) * 2001-06-11 2007-06-19 Xenoport, Inc. Methods for synthesis of acyloxyalkyl derivatives of GABA analogs
AU2002357506A1 (en) * 2001-12-25 2003-07-15 Takeda Chemical Industries, Ltd. Acid-containing preparations
US6927036B2 (en) 2002-02-19 2005-08-09 Xero Port, Inc. Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof
US7025745B2 (en) * 2002-10-07 2006-04-11 Advanced Cardiovascular Systems, Inc. Method of making a catheter balloon using a tapered mandrel
AU2003297909A1 (en) * 2002-12-11 2004-06-30 Xenoport, Inc. Orally administered dosage forms of fused gaba analog prodrugs having reduced toxicity
MXPA05006209A (es) * 2002-12-13 2005-08-19 Warner Lambert Co Pregabalina y sus derivados para el tratamiento de fibromialgia y otros trastornos relacionados.
CA2451267A1 (en) 2002-12-13 2004-06-13 Warner-Lambert Company Llc Pharmaceutical uses for alpha2delta ligands
DE60332387D1 (de) 2002-12-13 2010-06-10 Warner Lambert Co Alpha-2-delta-ligand zur behandlung vonsymptomen der unteren harnwege
US8641987B2 (en) 2003-01-24 2014-02-04 Applied Biosystems, Llc Sample chamber array and method for processing a biological sample
MXPA05010515A (es) 2003-03-31 2006-03-10 Xenoport Inc Tratamiento o prevencion de sofocos calientes utilizando profarmacos de analogos de gaba.
US7169812B2 (en) * 2003-07-01 2007-01-30 Medtronic, Inc. Process for producing injectable gabapentin compositions
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
KR20110097942A (ko) 2003-08-20 2011-08-31 제노포트 인코포레이티드 아실옥시알킬 카르바메이트 프로드러그, 합성 및 사용 방법
EP2354120A1 (en) * 2003-08-20 2011-08-10 XenoPort, Inc. Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof
KR20060119971A (ko) * 2003-09-11 2006-11-24 제노포트 인코포레이티드 Ｇａｂａ 유사체의 전구약물을 이용한 요실금의 치료및/또는 예방
DE602004024317D1 (de) 2003-09-12 2010-01-07 Pfizer Kombinationen aus alpha-2-delta liganden und serotonin / noradrenalin-wiederaufnahmehemmern
WO2005027850A2 (en) * 2003-09-17 2005-03-31 Xenoport, Inc. Treating or preventing restless legs syndrome using prodrugs of gaba analogs
RU2458049C2 (ru) * 2003-09-17 2012-08-10 Ксенопорт, Инк. Лечение или предупреждение синдрома беспокойных ног с использованием пролекарств аналогов гамк
MXPA06004088A (es) 2003-10-14 2006-06-27 Xenoport Inc Forma cristalina de un analogo del acido gamma-aminobutirico.
WO2005041976A2 (en) * 2003-10-23 2005-05-12 Medtronic, Inc. Injectable gabapentin compositions
ES2405329T3 (es) * 2003-12-30 2013-05-30 Xenoport, Inc. Síntesis de profármacos de carbarnato de aciloxialquilo y productos intermedios de los mismos
CN1902175B (zh) * 2003-12-30 2012-08-22 什诺波特有限公司 酰氧基烃基氨基甲酸酯前药及其中间体的合成
CA2570255A1 (en) * 2004-03-17 2005-09-22 Hikal Limited 4-t-butylgabapentin and its synthesis
CN1946391A (zh) * 2004-04-20 2007-04-11 辉瑞产品公司 包含α－2－δ配体的组合
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
EP1811986B1 (en) 2004-11-04 2014-03-26 XenoPort, Inc. Gabapentin prodrug sustained release oral dosage forms
JP2008530131A (ja) * 2005-02-15 2008-08-07 ジャズ、ファーマシューティカルズ、インコーポレイテッド 置換ピラジン化合物の徐放のための投薬形態および方法
US7351740B2 (en) * 2005-06-20 2008-04-01 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs of tranexamic acid, methods of synthesis and use
WO2007027477A2 (en) * 2005-08-23 2007-03-08 Xenoport, Inc. Treating vulvodynia using prodrugs of gaba analogs
US20070049626A1 (en) * 2005-08-26 2007-03-01 Tran Pierre V Treating premature ejaculation using gabapentin and pregabalin prodrugs
BRPI0615300A2 (pt) * 2005-08-31 2009-07-14 Wyeth Corp composto; composição farmacêutica; método para a preparação, tratamento ou controle de infecções bacterianas em animais de sangue quente; uso de um composto; e método para a preparação de compostos representados pela fórmula (i)
US7727978B2 (en) * 2006-08-24 2010-06-01 Bristol-Myers Squibb Company Cyclic 11-beta hydroxysteroid dehydrogenase type I inhibitors
US7585996B2 (en) 2006-09-15 2009-09-08 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs, methods of synthesis and use
US7879906B2 (en) 2006-11-24 2011-02-01 Anchen Laboratories, Inc. GABA analogs, compositions and methods for manufacturing thereof
US7632836B2 (en) * 2006-11-30 2009-12-15 Cenerx Biopharma, Inc. Dialkylamino alkyl esters of pivagabine as medicaments for the treatment of central nervous system disorders
BRPI0720252A2 (pt) * 2006-12-08 2014-01-07 Xenoport Inc Uso de pró-fármacos de análogos de gaba para tratar doenças
ATE511860T1 (de) 2006-12-22 2011-06-15 Recordati Ireland Ltd Kombinationstherapie für erkrankungen der unteren harnwege mit 2 liganden und nsar
WO2008157408A2 (en) * 2007-06-15 2008-12-24 Xenoport, Inc. Use of prodrugs of gaba analogs, antispasticity agents, and prodrugs of gaba b receptor agonists for treating spasticity
KR101307686B1 (ko) 2007-07-20 2013-09-12 아미리스 인코퍼레이티드 테트라메틸시클로헥산을 포함하는 연료 조성물
WO2009061934A1 (en) * 2007-11-06 2009-05-14 Xenoport, Inc. Use of prodrugs of gaba b agonists for treating neuropathic and musculoskeletal pain
WO2009094577A2 (en) 2008-01-25 2009-07-30 Xenoport, Inc. Mesophasic forms of (3s)-aminomethyl-5-methyl-hexanoic acid prodrugs and methods of use
US7872046B2 (en) 2008-01-25 2011-01-18 Xenoport, Inc. Crystalline form of a (3S)-aminomethyl-5-methyl-hexanoic acid prodrug and methods of use
EP2250143B1 (en) 2008-01-25 2016-04-20 XenoPort, Inc. Method for the enzymatic kinetic resolution of acyloxyalkyl thiocarbonates used for the synthesis of acyloxyalkyl carbamates
SG176464A1 (en) 2008-05-09 2011-12-29 Agency Science Tech & Res Diagnosis and treatment of kawasaki disease
WO2010017498A1 (en) 2008-08-07 2010-02-11 Xenoport, Inc. Methods of synthesizing n-hydroxysuccinimidyl carbonates
US8299291B2 (en) * 2008-08-07 2012-10-30 Xenoport, Inc. Methods of synthesizing 1-(acyloxy)-alkyl carbamate prodrugs
US8283487B2 (en) 2008-11-26 2012-10-09 Teva Pharmaceutical Industries Ltd. Processes for the preparation and purification of gabapentin enacarbil
US20110303570A1 (en) 2009-03-02 2011-12-15 Astellas Pharma Inc. Package of solid pharmaceutical preparation
AU2010221167B2 (en) * 2009-03-06 2014-04-03 Xenoport, Inc. Oral dosage forms having a high loading of a gabapentin prodrug
WO2011101245A1 (en) 2010-02-18 2011-08-25 Nicox S.A. Nitric oxide releasing compounds for the treatment of neuropathic pain
MX2013000946A (es) 2010-07-30 2013-02-27 Toray Industries Agente terapeutico o agente profilactico para el dolor neuropatico.
WO2013163889A1 (en) * 2012-05-03 2013-11-07 Dsm Ip Assets B.V. New intermediate compound for preparing vitamin b6
WO2014134005A2 (en) 2013-02-26 2014-09-04 Xenoport, Inc. Method of making 1-(acyloxy)-alkyl carbamate compounds
SI3066091T1 (sl) 2013-11-05 2019-09-30 Astrazeneca Ab NMDA antagonist predzdravila
US10213394B1 (en) 2018-02-15 2019-02-26 Osmotica Kereskedelmi és Szolgáltató Korlátolt Felelõsségû Társaság Composition and method for treating neurological disease
US10213393B1 (en) 2018-02-15 2019-02-26 Osmotica Kereskedelmi és Szolgáltató Korlátolt Feleõsségû Társaság Composition and method for treating neurological disease
US20190247331A1 (en) 2018-02-15 2019-08-15 Osmotica Kereskedelmi és Szolgáltató Korlátolt Felelõsségû Társaság Composition and method for treating neurological disease
WO2020074160A1 (en) * 2018-10-10 2020-04-16 Curovir Ab Condensed pyrimidine or pyridazine derivatives as antiviral agents
CN114306234A (zh) * 2021-12-23 2022-04-12 江苏百奥信康医药科技有限公司 一种含有加巴喷丁复合物的tpgs胶束口服液及其制备方法

Family Cites Families (126)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2002A (en) * 1841-03-12 Tor and planter for plowing
US2003A (en) * 1841-03-12 Improvement in horizontal windivhlls
US2996431A (en) * 1953-12-16 1961-08-15 Barry Richard Henry Friable tablet and process for manufacturing same
US3402240A (en) * 1957-06-25 1968-09-17 Pfizer & Co C Medicinal tablet and process of making same
US3139383A (en) * 1961-06-26 1964-06-30 Norton Co Encapsulated time release pellets and method for encapsulating the same
GB1364672A (en) 1971-06-09 1974-08-29 Beecham Group Ltd Penicillins
US3962414A (en) * 1972-04-27 1976-06-08 Alza Corporation Structured bioerodible drug delivery device
US3845770A (en) * 1972-06-05 1974-11-05 Alza Corp Osmatic dispensing device for releasing beneficial agent
US3811444A (en) * 1972-12-27 1974-05-21 Alza Corp Bioerodible ocular device
US3916899A (en) 1973-04-25 1975-11-04 Alza Corp Osmotic dispensing device with maximum and minimum sizes for the passageway
DE2336218C3 (de) * 1973-07-17 1985-11-14 Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz Orale Arzneiform
US3992414A (en) * 1973-12-20 1976-11-16 Lever Brothers Company Process for the preparation of selectively halogenated ketals
US3992518A (en) * 1974-10-24 1976-11-16 G. D. Searle & Co. Method for making a microsealed delivery device
GB1478759A (en) * 1974-11-18 1977-07-06 Alza Corp Process for forming outlet passageways in pills using a laser
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
US4087544A (en) 1974-12-21 1978-05-02 Warner-Lambert Company Treatment of cranial dysfunctions using novel cyclic amino acids
US4093709A (en) * 1975-01-28 1978-06-06 Alza Corporation Drug delivery devices manufactured from poly(orthoesters) and poly(orthocarbonates)
US4036064A (en) * 1975-09-11 1977-07-19 Gilford Instrument Laboratories, Inc. Pipette device
US4093571A (en) * 1976-01-14 1978-06-06 Celanese Corporation Process for making porous metal containing powder coating compositions
US4063064A (en) * 1976-02-23 1977-12-13 Coherent Radiation Apparatus for tracking moving workpiece by a laser beam
US4079038A (en) * 1976-03-05 1978-03-14 Alza Corporation Poly(carbonates)
US4066747A (en) * 1976-04-08 1978-01-03 Alza Corporation Polymeric orthoesters housing beneficial drug for controlled release therefrom
US4070347A (en) * 1976-08-16 1978-01-24 Alza Corporation Poly(orthoester) co- and homopolymers and poly(orthocarbonate) co- and homopolymers having carbonyloxy functionality
US4189571A (en) * 1978-02-07 1980-02-19 Fisons Limited Esters of cromoglycates
US4285987A (en) * 1978-10-23 1981-08-25 Alza Corporation Process for manufacturing device with dispersion zone
US4200098A (en) * 1978-10-23 1980-04-29 Alza Corporation Osmotic system with distribution zone for dispensing beneficial agent
FR2476087A1 (fr) * 1980-02-18 1981-08-21 Roussel Uclaf Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkyl-thiomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
JPS57193489A (en) * 1981-05-21 1982-11-27 Fujisawa Pharmaceut Co Ltd Syn-isomer of 7-substituted-3-cephem-4-carboxylic acid ester and its preparation
US4434153A (en) * 1982-03-22 1984-02-28 Alza Corporation Drug delivery system comprising a reservoir containing a plurality of tiny pills
US4421736A (en) * 1982-05-20 1983-12-20 Merrel Dow Pharmaceuticals Inc. Sustained release diethylpropion compositions
US4721613A (en) * 1982-12-13 1988-01-26 Alza Corporation Delivery system comprising means for shielding a multiplicity of reservoirs in selected environment of use
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
EP0130119B1 (en) * 1983-06-23 1988-11-09 Merck & Co. Inc. (acyloxyalkoxy) carbonyl derivatives as bioreversible prodrug moieties for primary and secondary amine functions in drugs, their preparation and pharmaceutical compositions containing said derivatives
EP0136893B1 (en) * 1983-10-05 1989-08-16 Merck Frosst Canada Inc. Benzo[a]phenothiazines and hydro-derivatives and pharmaceutical compositions containing them
US4611056A (en) * 1983-10-05 1986-09-09 Merck Frosst Canada, Inc. Benzo[A]phenothiazines and hydro-derivatives
DE3484745D1 (de) * 1983-10-05 1991-08-01 Merck Frosst Canada Inc Inhibitoren fuer die leukotrien-biosynthese.
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
US5051448A (en) * 1984-07-24 1991-09-24 The Mclean Hospital Corporation GABA esters and GABA analog esters
US4820523A (en) * 1986-04-15 1989-04-11 Warner-Lambert Company Pharmaceutical composition
US4752470A (en) * 1986-11-24 1988-06-21 Mehta Atul M Controlled release indomethacin
IL87710A (en) * 1987-09-18 1992-06-21 Ciba Geigy Ag Covered floating retard form for controlled release in gastric juice
US4816263A (en) * 1987-10-02 1989-03-28 Alza Corporation Dosage form for treating cardiovascular diseases comprising isradipine
US4853229A (en) * 1987-10-26 1989-08-01 Alza Corporation Method for adminstering tiny pills
DE3815221C2 (de) 1988-05-04 1995-06-29 Gradinger F Hermes Pharma Verwendung einer Retinol- und/oder Retinsäureester enthaltenden pharmazeutischen Zubereitung zur Inhalation zur Einwirkung auf die Schleimhäute des Tracheo-Bronchialtraktes einschließlich der Lungenalveolen
PH26730A (en) * 1988-12-30 1992-09-28 Ciba Geigy Ag Coated adhesive tablets
DE3928183A1 (de) 1989-08-25 1991-02-28 Goedecke Ag Lactamfreie cyclische aminosaeuren
US5084169A (en) * 1989-09-19 1992-01-28 The University Of Colorado Foundation, Inc. Stationary magnetically stabilized fluidized bed for protein separation and purification
US5084479A (en) * 1990-01-02 1992-01-28 Warner-Lambert Company Novel methods for treating neurodegenerative diseases
GB9001405D0 (en) * 1990-01-22 1990-03-21 Leo Pharm Prod Ltd New intermediates,their production and use
EP0458751A1 (en) * 1990-05-25 1991-11-27 Warner-Lambert Company Delivery system for cyclic amino acids with improved taste, texture and compressibility
JPH04103574A (ja) * 1990-08-22 1992-04-06 Kumiai Chem Ind Co Ltd ピリミジン誘導体及び除草剤
US5827819A (en) * 1990-11-01 1998-10-27 Oregon Health Sciences University Covalent polar lipid conjugates with neurologically active compounds for targeting
AU9137091A (en) 1990-11-27 1992-06-25 Northwestern University Gaba and l-glutamic acid analogs for antiseizure treatment
US6197819B1 (en) * 1990-11-27 2001-03-06 Northwestern University Gamma amino butyric acid analogs and optical isomers
TW209174B (enExample) * 1991-04-19 1993-07-11 Takeda Pharm Industry Co Ltd
US5698155A (en) * 1991-05-31 1997-12-16 Gs Technologies, Inc. Method for the manufacture of pharmaceutical cellulose capsules
GB9204918D0 (en) 1992-03-06 1992-04-22 Nycomed As Chemical compounds
RU94046105A (ru) * 1992-05-20 1997-06-20 Нортвестерн Юниверсити (Us) АНАЛОГИ γ -АМИНОМАСЛЯНОЙ КИСЛОТЫ И L-ГЛУТАМИНОВОЙ КИСЛОТЫ И СПОСОБЫ ИХ ПОЛУЧЕНИЯ
WO1993025197A1 (en) 1992-06-12 1993-12-23 Affymax Technologies N.V. Compositions and methods for enhanced drug delivery
JPH09503783A (ja) 1993-10-14 1997-04-15 アボツト・ラボラトリーズ キノリジノン型化合物
ZA953078B (en) * 1994-04-28 1996-01-05 Alza Corp Effective therapy for epilepsies
US5466811A (en) 1994-07-18 1995-11-14 Merck & Co., Inc. Dioxolenylmethyl carbamates pro moieties for amine drugs
US5684018A (en) 1994-12-13 1997-11-04 Merck & Co., Inc. Acyloxyisopropyl carbamates as prodrugs for amine drugs
US5672584A (en) * 1995-04-25 1997-09-30 The University Of Kansas Cyclic prodrugs of peptides and peptide nucleic acids having improved metabolic stability and cell membrane permeability
WO1996038435A1 (en) 1995-05-30 1996-12-05 Abbott Laboratories Dopamine agonists
HUP9901074A3 (en) 1996-02-07 2001-08-28 Warner Lambert Co Tetrahydropyrane and tetrahydrothiopyrane aminoacids and pharmaceutical compositions containing them
SK282848B6 (sk) 1996-03-14 2002-12-03 Warner-Lambert Company Premostené cyklické aminokyseliny, farmaceutická kompozícia obsahujúca tieto aminokyseliny
CZ293759B6 (cs) 1996-03-14 2004-07-14 Warner-Lambert Company Substituovaná cyklická aminokyselina, její použití a farmaceutický prostředek na její bázi
US6001876A (en) 1996-07-24 1999-12-14 Warner-Lambert Company Isobutylgaba and its derivatives for the treatment of pain
NZ333713A (en) 1996-07-30 2000-12-22 Axys Pharm Inc Compounds for treating diseases associated with tryptase activity
US5962473A (en) 1996-08-16 1999-10-05 Eli Lilly And Company Methods of treating or ameliorating the symptoms of common cold or allergic rhinitis with serotonin 5-HT1F
US6375987B1 (en) * 1996-10-01 2002-04-23 Gattefossé, S.A. Process for the manufacture of pharmaceutical composition with modified release of active principle comprising the matrix
NZ334898A (en) 1996-10-23 2000-09-29 Warner Lambert Co Substituted gamma aminobutyric acids as pharamceutical agents
EP1007037A4 (en) 1997-06-26 2004-10-06 Lilly Co Eli ANTITHROMBOTIC AGENTS
AU8668598A (en) 1997-08-20 1999-03-08 University Of Oklahoma, The Gaba analogs to prevent and treat gastrointestinal damage
US6127418A (en) * 1997-08-20 2000-10-03 Warner-Lambert Company GABA analogs to prevent and treat gastrointestinal damage
US6740682B2 (en) * 1997-08-29 2004-05-25 Tularik Limited Meta-benzamidine derivatives as serine protease inhibitors
KR100589066B1 (ko) 1997-10-27 2006-06-13 워너-램버트 캄파니 엘엘씨 약제로서 유용한 시클릭 아미노산 및 그의 유도체
ES2216338T3 (es) * 1997-12-16 2004-10-16 Warner-Lambert Company Llc Aminas novedosas como agentes farmaceuticos.
WO1999031075A1 (en) 1997-12-16 1999-06-24 Warner-Lambert Company 1-substituted-1-aminomethyl-cycloalkane derivatives (=gabapentin analogues), their preparation and their use in the treatment of neurological disorders
KR20010033153A (ko) 1997-12-16 2001-04-25 로즈 암스트롱, 크리스틴 에이. 트러트웨인 4(3)-치환-4(3)-아미노메틸-(티오)피란 또는 -피페리딘유도체(=가바펜틴 동족체), 그의 제법 및 신경 질환 치료용도
WO1999037296A1 (en) 1998-01-23 1999-07-29 Warner-Lambert Company Gabapentin and its derivatives for the treatment of muscular and skeletal pain
EP1082306A1 (en) 1998-05-26 2001-03-14 Warner-Lambert Company Conformationally constrained amino acid compounds having affinity for the alpha2delta subunit of a calcium channel
FR2779651B1 (fr) * 1998-06-16 2001-04-20 Gattefosse Ets Sa Procede pour la fabrication de comprimes a liberation prolongee de principe(s) actif(s) presentant une cinetique de dissolution d'ordre zero
US6171615B1 (en) * 1998-07-06 2001-01-09 Gattefoss{acute over (e)} Sustained release theophylline formulations, excipient systems and methods of production
CA2339273C (en) 1998-09-14 2005-10-18 Warner-Lambert Company Branched alkyl pyrrolidine-3-carboxylic acids
KR100697734B1 (ko) 1998-10-16 2007-03-22 워너-램버트 캄파니 엘엘씨 조증 및 양극성 장애 치료용 제약 조성물
CO5210925A1 (es) * 1998-11-17 2002-10-30 Novartis Ag Derivados de diamino nitroguanidina tetrasustituidos
AU1602100A (en) 1998-11-25 2000-06-13 Warner-Lambert Company Improved gamma amino butyric 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
BR0011006A (pt) 1999-05-27 2002-02-19 Pfizer Prod Inc Prõ-drogas mútuas de amlodipina e atorvastatina
CA2374755C (en) * 1999-06-10 2010-03-30 Warner-Lambert Company Mono- and disubstituted 3-propyl gamma-aminobutyric acids
HN2000000224A (es) * 1999-10-20 2001-04-11 Warner Lambert Co Aminoacidos biciclicos como agentes farmaceuticos
CZ20012758A3 (cs) 1999-12-08 2002-09-11 Warner-Lambert Company Větvené aminokyselinově dependentní aminotransferasové inhibitory a jejich použití při léčení diabetické retinopatie
JP2004501067A (ja) 2000-01-28 2004-01-15 ローム　アンド　ハース　カンパニー 高められた特性をもつ医薬
WO2001062242A1 (en) 2000-02-24 2001-08-30 Biocryst Pharmaceuticals, Inc. Prodrugs of substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors
EP1289965B1 (en) 2000-05-25 2005-10-26 F. Hoffmann-La Roche Ag Substituted 1-aminoalkyl-lactams and their use as muscarinic receptor antagonists
GB2362646A (en) * 2000-05-26 2001-11-28 Warner Lambert Co Cyclic amino acid derivatives useful as pharmaceutical agents
ATE390133T1 (de) 2000-06-26 2008-04-15 Warner Lambert Co Gabapentinanaloga für schlafstörungen
ATE321052T1 (de) 2000-07-07 2006-04-15 Novo Nordisk As Modulatoren von protein tyrosin phosphatasen (ptpasen)
AU2001268951A1 (en) 2000-07-07 2002-01-21 Novo-Nordisk A/S Modulators of protein tyrosine phosphatases (ptpases)
GB0018528D0 (en) 2000-07-27 2000-09-13 Photocure Asa Compounds
GB2365425A (en) * 2000-08-01 2002-02-20 Parke Davis & Co Ltd Alkyl amino acid derivatives useful as pharmaceutical agents
DZ3415A1 (fr) 2000-08-31 2002-03-07 Chiron Corp Guanidinobenzamides comme mc4-r agonistes.
AU2002243204A1 (en) 2000-10-06 2002-06-11 Xenoport, Inc. Bile-acid derived compounds for enhancing oral absorption and systemic bioavailability of drugs
AU2002211863A1 (en) 2000-10-06 2002-04-15 Xenoport, Inc. Bile-acid derived compounds for providing sustained systemic concentrations of drugs after oral administration
EP1361847A2 (en) 2000-10-06 2003-11-19 Xenoport, Inc. Bile-acid conjugates for providing sustained systemic concentrations of drugs
WO2002034711A1 (en) 2000-10-20 2002-05-02 Biocryst Pharmaceuticals, Inc. Biaryl compounds as serine protease inhibitors
US6683112B2 (en) * 2000-10-24 2004-01-27 Andrx Corporation Gabapentin prodrugs and formulations
GB2368579A (en) * 2000-10-31 2002-05-08 Parke Davis & Co Ltd Azole pharmaceutical agents
WO2002042414A2 (en) * 2000-11-17 2002-05-30 Xenoport, Inc. Amino acid conjugates providing for sustained systemic concentrations of gaba analogues
WO2002062766A2 (en) * 2001-02-07 2002-08-15 Millennium Pharmaceuticals, Inc. Melanocortin-4 receptor binding compounds and methods of use thereof
US20030031711A1 (en) 2001-05-29 2003-02-13 Fara John W. Method of treating gastroesophageal reflux disease and nocturnal acid breakthrough
MXPA03011566A (es) 2001-06-11 2004-10-28 Xenoport Inc Formas de dosificacion de profarmacos de analogos de gaba administrados oralmente que tienen toxicidad reducida.
US6818787B2 (en) * 2001-06-11 2004-11-16 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
GB0115517D0 (en) 2001-06-25 2001-08-15 Ferring Bv Novel antidiabetic agents
RU2325152C2 (ru) 2001-07-04 2008-05-27 Сан Фармасьютикл Индастриз Лимитид Удерживаемая в желудке система регулируемой доставки лекарственного средства
JP2004537544A (ja) 2001-07-13 2004-12-16 パラテック ファーマシューティカルズ インコーポレイテッド 標的治療活性を有するテトラサイクリン化合物
US7053076B2 (en) * 2001-08-29 2006-05-30 Xenoport, Inc. Bile-acid derived compounds for enhancing oral absorption and systemic bioavailability of drugs
US6723340B2 (en) * 2001-10-25 2004-04-20 Depomed, Inc. Optimal polymer mixtures for gastric retentive tablets
TWI312285B (en) 2001-10-25 2009-07-21 Depomed Inc Methods of treatment using a gastric retained gabapentin dosage
US20030158254A1 (en) * 2002-01-24 2003-08-21 Xenoport, Inc. Engineering absorption of therapeutic compounds via colonic transporters
US6927036B2 (en) * 2002-02-19 2005-08-09 Xero Port, Inc. Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof
US20050032135A1 (en) * 2003-07-03 2005-02-10 Xenoport, Inc. Monocarboxylate transporters expressed in cancer cells
WO2005121787A2 (en) * 2004-06-04 2005-12-22 Xenoport, Inc. Lat1 transporters expressed in cancer cells
TW200616604A (en) * 2004-08-26 2006-06-01 Nicholas Piramal India Ltd Nitric oxide releasing prodrugs containing bio-cleavable linker

Also Published As

Publication number Publication date
WO2002100347A2 (en) 2002-12-19
KR20090121404A (ko) 2009-11-25
KR20070108282A (ko) 2007-11-08
DE60223923D1 (de) 2008-01-17
MXPA03011566A (es) 2004-10-28
JP2004536873A (ja) 2004-12-09
ZA200309679B (en) 2005-02-23
EP1404324A4 (en) 2004-12-22
PT1404324E (pt) 2008-03-05
US20030083382A1 (en) 2003-05-01
AU2007203364B2 (en) 2010-07-29
EP1404310A1 (en) 2004-04-07
HK1129103A1 (en) 2009-11-20
WO2002100347A3 (en) 2003-10-16
CA2449729A1 (en) 2002-12-19
DK1404324T3 (da) 2008-03-31
US20040198820A1 (en) 2004-10-07
AU2002310409B2 (en) 2007-08-02
KR100958552B1 (ko) 2010-05-17
IL159299A0 (en) 2004-06-01
KR20040016882A (ko) 2004-02-25
JP2009051822A (ja) 2009-03-12
NO20083956L (no) 2004-02-09
DE60223923T2 (de) 2008-11-13
AU2008221505C1 (en) 2011-08-18
NO333756B1 (no) 2013-09-09
EP1902714B1 (en) 2012-01-11
EP1404310A4 (en) 2005-01-12
JP5001227B2 (ja) 2012-08-15
ATE380029T1 (de) 2007-12-15
WO2002100392A1 (en) 2002-12-19
KR100926921B1 (ko) 2009-11-17
CA2449729C (en) 2009-11-03
HUP0400183A2 (hu) 2004-07-28
IL159300A0 (en) 2004-06-01
IL159300A (en) 2011-06-30
AU2008221505A1 (en) 2008-10-09
JP2004534057A (ja) 2004-11-11
EP1902714A1 (en) 2008-03-26
EP1404324A2 (en) 2004-04-07
HUP0400167A3 (en) 2012-09-28
ES2296956T3 (es) 2008-05-01
IL197843A (en) 2011-06-30
KR20040029321A (ko) 2004-04-06
US6833140B2 (en) 2004-12-21
NO20035474D0 (no) 2003-12-09
CY1107894T1 (el) 2013-09-04
HK1087628A1 (en) 2006-10-20
HUP0400167A2 (hu) 2004-07-28
CA2449673A1 (en) 2002-12-19
EP1404324B2 (en) 2011-04-06
NO20083958L (no) 2004-02-09
CN1533270A (zh) 2004-09-29
ES2296956T5 (es) 2011-07-12
DE60223923T3 (de) 2013-05-16
DK1404324T4 (da) 2011-07-11
EP1404324B1 (en) 2007-12-05
AU2002310409C1 (en) 2008-04-17
AU2007203364A1 (en) 2007-08-09
NO20035473D0 (no) 2003-12-09
EP2085087A1 (en) 2009-08-05
JP2009040766A (ja) 2009-02-26
ATE540678T1 (de) 2012-01-15
AU2002345664C1 (en) 2008-03-06
IL213649A0 (en) 2011-07-31
NZ567711A (en) 2009-10-30
ES2380287T3 (es) 2012-05-10
AU2008221505B2 (en) 2011-01-06
MXPA03011565A (es) 2004-10-28
KR20090018729A (ko) 2009-02-20

Similar Documents

Publication Publication Date Title
JP5001227B2 (ja) Ｇａｂａ類似体のプロドラッグ、組成物およびその使用
US6972341B2 (en) Prodrugs of GABA analogs, compositions and uses thereof
AU2002345664B2 (en) Prodrugs of gaba analogs, compositions and uses thereof
US8168623B2 (en) Prodrugs of GABA analogs, compositions and uses thereof
US9238616B2 (en) Prodrugs of gaba analogs, compositions and uses thereof
AU2002345664A1 (en) Prodrugs of gaba analogs, compositions and uses thereof
CN1753673B (zh) Gaba类似物的前药、及其组合物和应用
HK1133389A (en) Prodrugs of gaba analogs, compositions and uses thereof
HK1087628B (en) Prodrugs of gaba analogs, compositions and uses thereof

Legal Events

Date Code Title Description
A871 Explanation of circumstances concerning accelerated examination

Free format text: JAPANESE INTERMEDIATE CODE: A871

Effective date: 20060724

A975 Report on accelerated examination

Free format text: JAPANESE INTERMEDIATE CODE: A971005

Effective date: 20060906

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20060912

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20061211

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20061218

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20070312

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20070626

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20070925

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20071002

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20080311

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20080630

A911 Transfer to examiner for re-examination before appeal (zenchi)

Free format text: JAPANESE INTERMEDIATE CODE: A911

Effective date: 20080929

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20081021

A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20081106

R150 Certificate of patent or registration of utility model

Ref document number: 4216713

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20111114

Year of fee payment: 3

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20111114

Year of fee payment: 3

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20121114

Year of fee payment: 4

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20121114

Year of fee payment: 4

A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

R153 Grant of patent term extension

Free format text: JAPANESE INTERMEDIATE CODE: R153

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20121114

Year of fee payment: 4

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20131114

Year of fee payment: 5

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

LAPS Cancellation because of no payment of annual fees
R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

EXPY Cancellation because of completion of term