PL194125B1 - Zastosowanie analogów GABA i kompozycja zawierająca analogi GABA - Google Patents
Zastosowanie analogów GABA i kompozycja zawierająca analogi GABAInfo
- Publication number
- PL194125B1 PL194125B1 PL98338705A PL33870598A PL194125B1 PL 194125 B1 PL194125 B1 PL 194125B1 PL 98338705 A PL98338705 A PL 98338705A PL 33870598 A PL33870598 A PL 33870598A PL 194125 B1 PL194125 B1 PL 194125B1
- Authority
- PL
- Poland
- Prior art keywords
- gabapentin
- group
- composition
- use according
- pharmaceutically acceptable
- Prior art date
Links
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- 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
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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Landscapes
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5675397P | 1997-08-20 | 1997-08-20 | |
| US7479498P | 1998-02-16 | 1998-02-16 | |
| US8293698P | 1998-04-24 | 1998-04-24 | |
| PCT/US1998/017082 WO1999008671A1 (en) | 1997-08-20 | 1998-08-18 | Gaba analogs to prevent and treat gastrointestinal damage |
Publications (2)
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| PL338705A1 PL338705A1 (en) | 2000-11-20 |
| PL194125B1 true PL194125B1 (pl) | 2007-04-30 |
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| PL98338705A PL194125B1 (pl) | 1997-08-20 | 1998-08-18 | Zastosowanie analogów GABA i kompozycja zawierająca analogi GABA |
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| EP (1) | EP1009399B1 (enExample) |
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| HU (1) | HUP0004551A3 (enExample) |
| IL (1) | IL134164A (enExample) |
| IS (1) | IS2749B (enExample) |
| MY (1) | MY155223A (enExample) |
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| US6001876A (en) | 1996-07-24 | 1999-12-14 | Warner-Lambert Company | Isobutylgaba and its derivatives for the treatment of pain |
| WO1999012537A1 (en) | 1997-09-08 | 1999-03-18 | Warner-Lambert Company | Analgesic compositions comprising anti-epileptic compounds and methods of using same |
| 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 |
| CA2359485A1 (en) | 1999-03-10 | 2000-09-14 | Warner-Lambert Company | Analgesic compositions comprising anti-epileptic compounds and methods of using same |
| US6992109B1 (en) * | 1999-04-08 | 2006-01-31 | Segal Catherine A | Method for the treatment of incontinence |
| WO2000061188A1 (en) * | 1999-04-09 | 2000-10-19 | Euro-Celtique S.A. | Sodium channel blocker compositions and the use thereof |
| EP1840117A1 (en) * | 1999-06-10 | 2007-10-03 | Warner-Lambert Company LLC | Mono- and disubstituted 3-propyl gamma-aminobutyric acids |
| DE60034344T2 (de) | 1999-07-22 | 2008-01-10 | University Of Rochester | Methode zur behandlung der symptome hormoneller veränderungen, einschliesslich hitzewallungen |
| FR2801217B1 (fr) * | 1999-11-24 | 2002-12-06 | Aventis Pharma Sa | Association de riluzole et de gabapentine et son utilisation comme medicament |
| CA2408246A1 (en) | 2000-05-16 | 2001-11-22 | Warner-Lambert Company | Cell line for the expression of an .alpha.2.delta.2 calcium channel subunit |
| EP1343805A4 (en) | 2000-10-06 | 2005-07-20 | Xenoport Inc | COMPOUNDS DERIVED FROM GALLENIC ACIDS FOR THE PROVISION OF CONTINUING SYSTEMIC CONCENTRATIONS OF MEDICINAL PRODUCTS AFTER ORAL ADMINISTRATION |
| US6900192B2 (en) | 2000-10-06 | 2005-05-31 | Xenoport, Inc. | Bile-acid conjugates for providing sustained systemic concentrations of drugs |
| EP1226820A1 (en) * | 2001-01-26 | 2002-07-31 | Warner-Lambert Company | Use of bicyclic amino acids for preventing and treating visceral pain and gastrointestinal disorders |
| 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 |
| PT1404324E (pt) | 2001-06-11 | 2008-03-05 | Xenoport Inc | Formas de dosagem administradas oralmente de pró-fármacos análogas de gaba tendo toxicidade reduzida |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| AU2002345638A1 (en) | 2001-06-11 | 2002-12-23 | Xenoport, Inc. | Amino acid conjugates providing for sustained systemic concentrations of gaba analogues |
| US7232924B2 (en) | 2001-06-11 | 2007-06-19 | Xenoport, Inc. | Methods for synthesis of acyloxyalkyl derivatives of GABA analogs |
| ATE317280T1 (de) | 2001-09-03 | 2006-02-15 | Newron Pharm Spa | Pharmazeutische zusammensetzung mit gabapentin oder deren analog und einem alpha-aminoamid und analgetische verwendung dieser zusammensetzung |
| US20060159743A1 (en) * | 2001-10-25 | 2006-07-20 | Depomed, Inc. | Methods of treating non-nociceptive pain states with gastric retentive gabapentin |
| TWI312285B (en) | 2001-10-25 | 2009-07-21 | Depomed Inc | Methods of treatment using a gastric retained gabapentin dosage |
| US7612112B2 (en) * | 2001-10-25 | 2009-11-03 | Depomed, Inc. | Methods of treatment using a gastric retained gabapentin dosage |
| US20070184104A1 (en) * | 2001-10-25 | 2007-08-09 | Depomed, Inc. | Gastric retentive gabapentin dosage forms and methods for using same |
| AU2002316231A1 (en) | 2002-02-19 | 2003-09-29 | Xenoport, Inc. | Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof |
| WO2003070237A1 (en) * | 2002-02-22 | 2003-08-28 | Warner-Lambert Company Llc | Combinations of an alpha-2-delta ligand with a selective inhibitor of cyclooxygenase-2 |
| US7026351B2 (en) | 2002-03-20 | 2006-04-11 | Xenoport, Inc. | 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 |
| JP2005533100A (ja) * | 2002-07-10 | 2005-11-04 | 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、カンパニー | Gaba誘導体を含む胃腸用組成物 |
| US7025745B2 (en) * | 2002-10-07 | 2006-04-11 | Advanced Cardiovascular Systems, Inc. | Method of making a catheter balloon using a tapered mandrel |
| US20040105881A1 (en) * | 2002-10-11 | 2004-06-03 | Gregor Cevc | Aggregates with increased deformability, comprising at least three amphipats, for improved transport through semi-permeable barriers and for the non-invasive drug application in vivo, especially through the skin |
| US7060727B2 (en) | 2002-12-11 | 2006-06-13 | Xenoport, Inc. | Prodrugs of fused GABA analogs, pharmaceutical compositions and uses thereof |
| NZ567457A (en) * | 2002-12-13 | 2009-08-28 | Warner Lambert Co | Alpha-2-delta ligand to treat lower urinary tract symptoms |
| 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 |
| WO2004078734A1 (en) | 2003-03-07 | 2004-09-16 | Warner-Lambert Company Llc | TETRAZOLE AND OXADIAZOLONE SUBSTITUTED β-AMINO ACID DERIVATIVES |
| WO2004084881A1 (en) * | 2003-03-21 | 2004-10-07 | Dynogen Pharmaceuticals, Inc. | METHODS FOR TREATING FUNCTIONAL BOWEL DISORDERS USING α2δ SUBUNIT CALCIUM CHANNEL MODULATORS WITH SMOOTH MUSCLE MODULATORS |
| US20050043407A1 (en) * | 2003-08-22 | 2005-02-24 | Pfizer Inc | Pharmaceutical composition for the prevention and treatment of addiction in a mammal |
| EP1670451A4 (en) | 2003-09-11 | 2009-10-21 | Xenoport Inc | TREATMENT AND / OR PREVENTION OF URINARY INCONTINENCE AND PROMOTERS OF GABA ANALOGS |
| WO2005027850A2 (en) | 2003-09-17 | 2005-03-31 | Xenoport, Inc. | Treating or preventing restless legs syndrome using prodrugs of gaba analogs |
| KR101096480B1 (ko) | 2003-10-14 | 2011-12-20 | 제노포트 인코포레이티드 | 감마-아미노부티르산 유사체의 결정질 형태 |
| PL1691811T3 (pl) | 2003-12-11 | 2014-12-31 | Sunovion Pharmaceuticals Inc | Skojarzenie leku uspokajającego i modulatora neuroprzekaźnikowego oraz sposoby poprawy jakości snu i leczenia depresji |
| RU2335342C2 (ru) * | 2004-03-12 | 2008-10-10 | Уорнер-Ламберт Компани Ллс | C1-симметричные бисфосфиновые лиганды и их применение в асимметрическом синтезе прегабалина |
| JP2007530657A (ja) * | 2004-04-01 | 2007-11-01 | 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 | Pキラル性ホスホランの調製および不斉合成でのその使用 |
| EA200800909A1 (ru) | 2004-06-21 | 2008-08-29 | УОРНЕР-ЛАМБЕРТ КОМПАНИ ЭлЭлСи | Получение прегабалина и родственных соединений |
| SI1809271T1 (sl) * | 2004-09-10 | 2010-10-29 | Newron Pharm Spa | Uporaba (R)-(halobenziloksi) benzilamino propanamidov kot selektivnih modulatorjev natrijevih in/ali kalcijevih kanalov |
| US8795725B2 (en) | 2004-11-04 | 2014-08-05 | Xenoport, Inc. | GABA analog prodrug sustained release oral dosage forms |
| EP1963280B1 (en) | 2005-12-22 | 2015-10-28 | Newron Pharmaceuticals S.p.A. | 2-phenylethylamino derivatives as calcium and/or sodium channel modulators |
| US20090176882A1 (en) * | 2008-12-09 | 2009-07-09 | Depomed, Inc. | Gastric retentive gabapentin dosage forms and methods for using same |
| EA200970487A1 (ru) * | 2006-12-08 | 2009-12-30 | Ксенопорт, Инк. | Применение пролекарств аналогов гамк для лечения заболеваний |
| CA2703472A1 (en) * | 2007-10-26 | 2009-04-30 | The Scripps Research Institute | Methods for treating substance dependence |
| WO2009094577A2 (en) | 2008-01-25 | 2009-07-30 | Xenoport, Inc. | Mesophasic forms of (3s)-aminomethyl-5-methyl-hexanoic acid prodrugs and methods of use |
| JP5563483B2 (ja) | 2008-01-25 | 2014-07-30 | ゼノポート,インコーポレイティド | アシロキシアルキルカルバメートプロドラッグの合成に使用されるアシロキシアルキルチオカーボネートの鏡像異性的な分解 |
| 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 |
| SG157299A1 (en) | 2008-05-09 | 2009-12-29 | Agency Science Tech & Res | Diagnosis and treatment of kawasaki disease |
| ES2589915T3 (es) | 2008-10-08 | 2016-11-17 | Xgene Pharmaceutical Inc | Conjugados de GABA y métodos de utilización de los mismos |
| CN104922084B (zh) * | 2009-06-22 | 2020-01-14 | 惠氏有限责任公司 | 布洛芬钠片剂和制备包含布洛芬钠的药物组合物的方法 |
| WO2011141923A2 (en) | 2010-05-14 | 2011-11-17 | Lupin Limited | Improved synthesis of optically pure (s) - 3-cyano-5-methyl-hexanoic acid alkyl ester, an intermediate of (s)- pregabalin |
| WO2012059797A1 (en) | 2010-11-04 | 2012-05-10 | Lupin Limited | Process for synthesis of (s) - pregabalin |
| US9066853B2 (en) | 2013-01-15 | 2015-06-30 | Warsaw Orthopedic, Inc. | Clonidine compounds in a biodegradable fiber |
| AU2014209028C1 (en) | 2013-01-28 | 2019-08-29 | Hector L. Lopez | Methods of improving tolerability, pharmacodynamics, and efficacy of b-alanine and use therefor |
| CN105997970A (zh) * | 2015-12-16 | 2016-10-12 | 南昌大学 | γ-氨基丁酸在制备胃粘膜保护剂中的应用 |
| US10874626B2 (en) | 2016-04-07 | 2020-12-29 | Nevakar Inc. | Formulation for use in a method of treatment of pain |
| WO2019070641A1 (en) | 2017-10-03 | 2019-04-11 | Nevakar Inc. | COMBINATIONS OF ACETAMINOPHENE-PRÉGABALINE AND METHODS OF TREATING PAIN |
| EP4227293A3 (en) | 2018-05-14 | 2023-10-04 | Xgene Pharmaceutical Inc | Crystalline forms of 1-(acyloxy)-alkyl carbamate drug conjugates of naproxen and pregabalin |
| CN116999560A (zh) * | 2022-04-30 | 2023-11-07 | 武汉思瓴生物科技有限公司 | 可治疗疼痛的药物组合及其应用 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE634102A (enExample) | ||||
| DE1963925C3 (de) | 1969-12-20 | 1975-07-10 | Desitin-Werk, Carl Klinke Gmbh, 2000 Hamburg | Verfahren zur Herstellung von N hoch 3-Carbalkoxyderivaten des 5,5-Diphenylhydantoins |
| JPS54110334A (en) | 1978-02-16 | 1979-08-29 | Fuji Chem Ind Co Ltd | Novel compounded anodyne and antiiinflammatory agent |
| US4158581A (en) | 1978-04-14 | 1979-06-19 | Westinghouse Electric Corp. | Method of making magnetic component for direct current apparatus |
| JPS61221121A (ja) | 1985-03-27 | 1986-10-01 | Nitto Electric Ind Co Ltd | テ−プ製剤 |
| US4694010A (en) | 1985-08-16 | 1987-09-15 | New York University | Anticonvulsant compositions and method |
| EP0346445A4 (en) | 1987-12-22 | 1990-03-28 | Ferkany John W | DEXTRORPHANE POTENTIALIZER FOR ANTISPASMODIC COMPOSITIONS AND METHODS. |
| AU9137091A (en) | 1990-11-27 | 1992-06-25 | Northwestern University | Gaba and l-glutamic acid analogs for antiseizure treatment |
| GB9108362D0 (en) | 1991-04-18 | 1991-06-05 | Radoslavov Alexander | A pharmaceutical composition suitable for alleviation of headaches,migraine and other painful conditions |
| CZ286106B6 (cs) * | 1992-05-20 | 2000-01-12 | Northwestern University | Analogy GABA a L-glutamové kyseliny |
| US5234929A (en) | 1992-07-20 | 1993-08-10 | William Chelen | Method of treating motion sickness with anticonvulsants and antitussive agents |
| JPH06100468A (ja) | 1992-09-25 | 1994-04-12 | Kibun Food Chemifa Co Ltd | 徐放性組成物 |
| US5321012A (en) | 1993-01-28 | 1994-06-14 | Virginia Commonwealth University Medical College | Inhibiting the development of tolerance to and/or dependence on a narcotic addictive substance |
| JPH06227969A (ja) | 1993-02-02 | 1994-08-16 | Masayasu Sugihara | 薬品の腸溶性改善方法およびそれにより得られた薬品組成物 |
| US5420270A (en) | 1993-10-07 | 1995-05-30 | G. D. Searle & Co. | Aryl substituted dibenzoxazepine compounds, pharmaceutical compositions and methods of use |
| US5352638A (en) | 1994-02-22 | 1994-10-04 | Corning Incorporated | Nickel aluminosilicate glass-ceramics |
| CA2197463A1 (en) | 1994-09-02 | 1996-03-14 | David J. Mayer | Composition alleviating pain, containing a non-narcotic analgesic and an analgesia enhancer |
| GB9420784D0 (en) * | 1994-10-14 | 1994-11-30 | Glaxo Group Ltd | Medicaments |
| CN1046199C (zh) | 1994-12-13 | 1999-11-10 | 凌吉安 | 复方消炎止痛霜剂 |
| DE69733081T2 (de) * | 1996-08-23 | 2006-05-11 | Endo Pharmaceuticals Inc. (n.d.Ges.d. Staates Delaware) | Antikonvulsive mitteln enthaltende zubereitung zur behandlung von neuropathischen schmerzen |
| SE9603408D0 (sv) * | 1996-09-18 | 1996-09-18 | Astra Ab | Medical use |
| AU733896B2 (en) * | 1996-10-23 | 2001-05-31 | Warner-Lambert Company | Substituted gamma aminobutyric acids as pharmaceutical agents |
| US6127418A (en) * | 1997-08-20 | 2000-10-03 | Warner-Lambert Company | GABA analogs to prevent and treat gastrointestinal damage |
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