JP3909842B2 - 睡眠障害のためのガバペンチン類似物 - Google Patents
睡眠障害のためのガバペンチン類似物 Download PDFInfo
- Publication number
- JP3909842B2 JP3909842B2 JP2002504991A JP2002504991A JP3909842B2 JP 3909842 B2 JP3909842 B2 JP 3909842B2 JP 2002504991 A JP2002504991 A JP 2002504991A JP 2002504991 A JP2002504991 A JP 2002504991A JP 3909842 B2 JP3909842 B2 JP 3909842B2
- Authority
- JP
- Japan
- Prior art keywords
- aminomethyl
- acetic acid
- cyclopentyl
- methyl
- cyclobutyl
- 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 - Fee Related
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- 208000019116 sleep disease Diseases 0.000 title claims 3
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical class OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 title 1
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- 239000003814 drug Substances 0.000 claims description 11
- 206010022437 insomnia Diseases 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- IUVMAUQEZFTTFB-YUMQZZPRSA-N Atagabalin Chemical compound C[C@H]1CC(CN)(CC(O)=O)C[C@@H]1C IUVMAUQEZFTTFB-YUMQZZPRSA-N 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 170
- 150000001875 compounds Chemical class 0.000 description 29
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
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- 239000004480 active ingredient Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
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- 239000002775 capsule Substances 0.000 description 6
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000000147 hypnotic effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
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- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
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- DNHPJOLWCOXHOV-JTQLQIEISA-N 2-[(1r)-1-(aminomethyl)-2,2-dimethylcyclopentyl]acetic acid Chemical compound CC1(C)CCC[C@@]1(CN)CC(O)=O DNHPJOLWCOXHOV-JTQLQIEISA-N 0.000 description 1
- SIKUEILNNOXUAZ-LBPRGKRZSA-N 2-[(1r)-1-(aminomethyl)-3,3-diethylcyclopentyl]acetic acid Chemical compound CCC1(CC)CC[C@](CN)(CC(O)=O)C1 SIKUEILNNOXUAZ-LBPRGKRZSA-N 0.000 description 1
- QZBKCCCUSMQVTC-JTQLQIEISA-N 2-[(1r)-1-(aminomethyl)-3,3-dimethylcyclopentyl]acetic acid Chemical compound CC1(C)CC[C@](CN)(CC(O)=O)C1 QZBKCCCUSMQVTC-JTQLQIEISA-N 0.000 description 1
- OPAXRDNEIABTQI-SECBINFHSA-N 2-[(1s)-1-(aminomethyl)-2,2-dimethylcyclobutyl]acetic acid Chemical compound CC1(C)CC[C@]1(CN)CC(O)=O OPAXRDNEIABTQI-SECBINFHSA-N 0.000 description 1
- DNHPJOLWCOXHOV-SNVBAGLBSA-N 2-[(1s)-1-(aminomethyl)-2,2-dimethylcyclopentyl]acetic acid Chemical compound CC1(C)CCC[C@]1(CN)CC(O)=O DNHPJOLWCOXHOV-SNVBAGLBSA-N 0.000 description 1
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- 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
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- 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
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Engineering & Computer Science (AREA)
- Anesthesiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| US21417100P | 2000-06-26 | 2000-06-26 | |
| PCT/US2001/016343 WO2002000209A2 (en) | 2000-06-26 | 2001-05-18 | Gabapentin analogues for sleep disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004501189A JP2004501189A (ja) | 2004-01-15 |
| JP2004501189A5 JP2004501189A5 (https=) | 2006-06-22 |
| JP3909842B2 true JP3909842B2 (ja) | 2007-04-25 |
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| JP (1) | JP3909842B2 (https=) |
| KR (1) | KR100785182B1 (https=) |
| CN (1) | CN1279900C (https=) |
| AT (1) | ATE390133T1 (https=) |
| AU (2) | AU6473601A (https=) |
| BR (1) | BR0111913A (https=) |
| CA (1) | CA2414008C (https=) |
| CZ (1) | CZ20024110A3 (https=) |
| DE (1) | DE60133389T2 (https=) |
| DK (1) | DK1296671T3 (https=) |
| ES (1) | ES2300332T3 (https=) |
| HU (1) | HUP0300833A3 (https=) |
| IL (2) | IL152770A0 (https=) |
| MX (1) | MXPA02010668A (https=) |
| NZ (1) | NZ522480A (https=) |
| PL (1) | PL359872A1 (https=) |
| PT (1) | PT1296671E (https=) |
| SK (1) | SK17922002A3 (https=) |
| TW (1) | TWI298020B (https=) |
| WO (1) | WO2002000209A2 (https=) |
| ZA (1) | ZA200209418B (https=) |
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| SK12822003A3 (sk) | 2001-04-19 | 2004-04-06 | Warner - Lambert Company Llc | Fúzne bicyklické alebo tricyklické aminokyseliny |
| US6818787B2 (en) | 2001-06-11 | 2004-11-16 | 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 |
| US7186855B2 (en) | 2001-06-11 | 2007-03-06 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| ATE540678T1 (de) | 2001-06-11 | 2012-01-15 | Xenoport Inc | Prodrugs aus gaba-analoga, zusammensetzungen und ihre verwendungen |
| US7420002B2 (en) | 2001-06-11 | 2008-09-02 | Xenoport | Amino acid conjugates providing for sustained systemic concentrations of GABA analogues |
| WO2003077902A1 (en) | 2002-02-19 | 2003-09-25 | Xenoport, Inc. | Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof |
| AU2003222033A1 (en) | 2002-03-20 | 2003-10-08 | Xenoport | Cyclic 1-(acyloxy)-alkyl prodrugs of gaba analogs, compositions and uses thereof |
| WO2003099338A2 (en) | 2002-05-17 | 2003-12-04 | Xenoport, Inc. | Amino acid conjugates providing for sustained systemic concentrations of gaba analogues |
| WO2004052360A1 (en) | 2002-12-11 | 2004-06-24 | Xenoport, Inc. | Prodrugs of fused gaba analogs, pharmaceutical compositions and uses thereof |
| CA2451267A1 (en) * | 2002-12-13 | 2004-06-13 | Warner-Lambert Company Llc | Pharmaceutical uses for alpha2delta ligands |
| PL377286A1 (pl) * | 2002-12-13 | 2006-01-23 | Warner-Lambert Company Llc | Analogi gabapentyny do włókniako-mięśniakowych i innych pokrewnych zaburzeń |
| EP1622603A4 (en) * | 2003-03-25 | 2010-03-24 | Kiel Lab Inc | GABAPENTINIC PHENOLIC ACID SALTS IN SOLID DOSAGE FORMS AND METHODS OF USE |
| KR20060119971A (ko) | 2003-09-11 | 2006-11-24 | 제노포트 인코포레이티드 | Ｇａｂａ 유사체의 전구약물을 이용한 요실금의 치료및/또는 예방 |
| AU2004274002B2 (en) | 2003-09-17 | 2011-04-28 | Arbor Pharmaceuticals, Llc | Treating or preventing restless legs syndrome using prodrugs of GABA analogs |
| PT1677767E (pt) | 2003-10-14 | 2011-10-13 | Xenoport Inc | Forma cristalina de análogo de ácido gama-aminobutírico |
| JP4613031B2 (ja) * | 2004-05-06 | 2011-01-12 | エスエス製薬株式会社 | 催眠剤組成物 |
| JP2005325070A (ja) * | 2004-05-14 | 2005-11-24 | Ss Pharmaceut Co Ltd | 睡眠改善剤 |
| CA2584338C (en) | 2004-11-04 | 2013-08-06 | Xenoport, Inc. | Gabapentin prodrug sustained release oral dosage forms |
| US7837982B2 (en) | 2005-06-23 | 2010-11-23 | Emory University | Imaging agents |
| KR20070070307A (ko) * | 2005-08-24 | 2007-07-04 | 에스에스 세야쿠 가부시키 가이샤 | 수면 개선 의약 조성물 |
| CN101420947A (zh) * | 2006-03-06 | 2009-04-29 | 辉瑞产品公司 | 用于非恢复性睡眠的α-2-δ配体 |
| EP2250148B1 (en) | 2008-01-25 | 2016-08-17 | XenoPort, Inc. | Crystalline form of calcium-salts of (3s)-aminomethyl-5-methyl-hexanoic acids and methods of use |
| US7868043B2 (en) | 2008-01-25 | 2011-01-11 | Xenoport, Inc. | Mesophasic forms of (3S)-aminomethyl-5-methyl-hexanoic acid prodrugs and methods of use |
| CA2706575C (en) | 2008-01-25 | 2015-07-14 | Xenoport, Inc. | Enantiomerically resolving acyloxyalkyl thiocarbonates used in synthesizing acyloxyalkyl carbamate prodrugs |
| CN105330603A (zh) | 2008-10-08 | 2016-02-17 | 凯飞药业公司 | Gaba偶联物及其使用方法 |
| EP2509596B1 (en) | 2009-12-08 | 2019-08-28 | Case Western Reserve University | Gamma aminoacids for treating ocular disorders |
| US9066853B2 (en) | 2013-01-15 | 2015-06-30 | Warsaw Orthopedic, Inc. | Clonidine compounds in a biodegradable fiber |
| CA2903000C (en) | 2013-01-28 | 2021-10-12 | Hector L. Lopez | Methods of improving tolerability, pharmacodynamics, and efficacy of .beta.-alanine and use therefor |
| KR20240155382A (ko) * | 2016-05-26 | 2024-10-28 | 가부시키가이샤 아미노 압 | 수면 개선제 |
| CN112424158A (zh) | 2018-05-14 | 2021-02-26 | 昌郁医药公司 | 萘普生和普瑞巴林的1-(酰氧基)-烷基氨基甲酸酯药物缀合物的结晶形式 |
| CN117776950B (zh) * | 2022-09-20 | 2025-12-23 | 中科中山药物创新研究院 | 一种γ-氨基丁酸衍生物、药物组合物和应用 |
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| 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 |
| US5084479A (en) | 1990-01-02 | 1992-01-28 | Warner-Lambert Company | Novel methods for treating neurodegenerative diseases |
| US6197819B1 (en) | 1990-11-27 | 2001-03-06 | Northwestern University | Gamma amino butyric acid analogs and optical isomers |
| US5510381A (en) | 1995-05-15 | 1996-04-23 | Warner-Lambert Company | Method of treatment of mania and bipolar disorder |
| DE19525598C2 (de) * | 1995-07-13 | 1997-09-25 | Max Planck Gesellschaft | Schlafmittel |
| WO1997033859A1 (en) * | 1996-03-14 | 1997-09-18 | Warner-Lambert Company | Novel bridged cyclic amino acids as pharmaceutical agents |
| US6372792B1 (en) * | 1996-04-26 | 2002-04-16 | Guy Chouinard | Method for treating anxiety, anxiety disorders and insomnia |
| ATE323067T1 (de) * | 1997-10-27 | 2006-04-15 | Warner Lambert Co | Zyklische aminosäuren und deren derivate als arzneimittel |
| WO2000002546A2 (en) | 1998-07-09 | 2000-01-20 | Warner-Lambert Company | Use of caba-analogues for treating insomnia |
| PT1187832E (pt) * | 1999-06-02 | 2003-03-31 | Warner Lambert Co | Amino heterociclos uteis como agentes farmaceuticos |
| HN2000000224A (es) * | 1999-10-20 | 2001-04-11 | Warner Lambert Co | Aminoacidos biciclicos como agentes farmaceuticos |
| CN1607201A (zh) * | 1999-12-08 | 2005-04-20 | 沃尼尔·朗伯公司 | 立体选择性地合成环状氨基酸的方法 |
| GB9930083D0 (en) * | 1999-12-20 | 2000-02-09 | Glaxo Group Ltd | Medicaments |
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- 2001-05-18 DE DE60133389T patent/DE60133389T2/de not_active Expired - Lifetime
- 2001-05-18 WO PCT/US2001/016343 patent/WO2002000209A2/en not_active Ceased
- 2001-05-18 PT PT01939192T patent/PT1296671E/pt unknown
- 2001-05-18 KR KR1020027017609A patent/KR100785182B1/ko not_active Expired - Fee Related
- 2001-05-18 EP EP01939192A patent/EP1296671B1/en not_active Expired - Lifetime
- 2001-05-18 JP JP2002504991A patent/JP3909842B2/ja not_active Expired - Fee Related
- 2001-05-18 SK SK1792-2002A patent/SK17922002A3/sk not_active Application Discontinuation
- 2001-05-18 US US10/297,827 patent/US7141606B2/en not_active Expired - Fee Related
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- 2001-05-18 MX MXPA02010668A patent/MXPA02010668A/es active IP Right Grant
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