HRP20040891A2 - Amino acids with affinity for the alpha-2-delta-protein - Google Patents
Amino acids with affinity for the alpha-2-delta-proteinInfo
- Publication number
- HRP20040891A2 HRP20040891A2 HRP20040891A HRP20040891A2 HR P20040891 A2 HRP20040891 A2 HR P20040891A2 HR P20040891 A HRP20040891 A HR P20040891A HR P20040891 A2 HRP20040891 A2 HR P20040891A2
- Authority
- HR
- Croatia
- Prior art keywords
- acid
- alkyl
- amino
- phenyl
- pyridyl
- Prior art date
Links
- 150000001413 amino acids Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 179
- 150000003839 salts Chemical class 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 69
- 125000001153 fluoro group Chemical group F* 0.000 claims description 55
- 208000002193 Pain Diseases 0.000 claims description 45
- -1 phenyl-(C1-C3)alkyl Chemical group 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000004076 pyridyl group Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- VCOJPHSIBVJVDU-UHFFFAOYSA-N 2-(aminomethyl)-4,4,8-trimethylnonanoic acid Chemical compound CC(C)CCCC(C)(C)CC(CN)C(O)=O VCOJPHSIBVJVDU-UHFFFAOYSA-N 0.000 claims description 9
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- IVYDEZGCXPEAHO-HTQZYQBOSA-N (2r,4r)-2-(aminomethyl)-4-methylheptanoic acid Chemical compound CCC[C@@H](C)C[C@H](CN)C(O)=O IVYDEZGCXPEAHO-HTQZYQBOSA-N 0.000 claims description 4
- KFUYJCLUBOFHHM-UHFFFAOYSA-N 2-(aminomethyl)-3-(1-methylcyclopropyl)propanoic acid Chemical compound NCC(C(O)=O)CC1(C)CC1 KFUYJCLUBOFHHM-UHFFFAOYSA-N 0.000 claims description 4
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- ZTOJKCGCPJHZPN-UHFFFAOYSA-N 2-(aminomethyl)-3-[1-(4-methylpentyl)cyclopropyl]propanoic acid Chemical compound CC(C)CCCC1(CC(CN)C(O)=O)CC1 ZTOJKCGCPJHZPN-UHFFFAOYSA-N 0.000 claims description 3
- JVYGCKSEDCBNBD-UHFFFAOYSA-N 2-(aminomethyl)-4-ethyl-8-methylnonanoic acid Chemical compound NCC(C(O)=O)CC(CC)CCCC(C)C JVYGCKSEDCBNBD-UHFFFAOYSA-N 0.000 claims description 3
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DE10129693A1 (de) * | 2001-06-22 | 2003-01-02 | Jan Loock | Verfahren zur extrakorporalen qualitativen und/oder quantitativen Erfassung neurotoxischer Substanzen im Blutplasma eines Individuums |
NI200300043A (es) * | 2002-03-28 | 2003-11-05 | Warner Lambert Co | AMINOACIDOS CON AFINIDAD POR LA PROTEINA a2DELTA. |
US7419981B2 (en) | 2002-08-15 | 2008-09-02 | Pfizer Inc. | Synergistic combinations of an alpha-2-delta ligand and a cGMP phosphodieterse 5 inhibitor |
CA2451267A1 (en) | 2002-12-13 | 2004-06-13 | Warner-Lambert Company Llc | Pharmaceutical uses for alpha2delta ligands |
WO2005002585A1 (en) * | 2003-07-02 | 2005-01-13 | Warner-Lambert Company Llc | Combination of an allosteric inhibitor of matrix metalloproteinase-13 and a ligand to an alpha-2-delta receptor |
KR20070039986A (ko) * | 2003-09-25 | 2007-04-13 | 워너-램버트 캄파니 엘엘씨 | 알파2델타-단백질에 대한 친화성을 갖는 아미노산 |
WO2005030184A2 (en) * | 2003-09-25 | 2005-04-07 | Warner-Lambert Company Llc | Therapeutic beta aminoacids |
DE602005002253T2 (de) * | 2004-03-12 | 2008-05-29 | Warner-Lambert Company Llc | C1-symmetrische bisphosphinliganden und deren verwendung bei der asymmetrischen synthese von pregabalin |
AU2005264036A1 (en) * | 2004-07-09 | 2006-01-26 | Warner-Lambert Company Llc | Preparation of beta-amino acids having affinity for the alpha-2-delta protein |
WO2006092692A1 (en) * | 2005-03-01 | 2006-09-08 | Pfizer Limited | Use of combinations of pde7 inhibitors and alpha-2-delty ligands for the treatment of neuropathic pain |
EP1863780A1 (en) * | 2005-03-24 | 2007-12-12 | Pharmacia & Upjohn Company LLC | Preparation of optically pure beta-amino acids having affinity for the alpha-2-delta protein |
WO2007052134A1 (en) * | 2005-11-04 | 2007-05-10 | Pfizer Limited | (2s)-2-aminomethyl-5-ethyl heptanoic acid its pharmaceutical use |
CA2629896A1 (en) * | 2005-11-17 | 2007-05-24 | Pfizer Limited | Isocystene derivatives for the treatment of pain |
AU2007222112A1 (en) * | 2006-03-06 | 2007-09-13 | Pfizer Products Inc. | Alpha-2-delta ligands for non-restorative sleep |
AR061728A1 (es) * | 2006-06-30 | 2008-09-17 | Pfizer Prod Inc | Composicion para tratamiento usando compuestos selectivos alfa-2-delta-1 |
US20110124705A1 (en) * | 2009-11-24 | 2011-05-26 | Xenoport, Inc. | Prodrugs of alpha-2-delta ligands, pharmaceutical compositions and uses thereof |
AU2012255759B2 (en) | 2011-05-17 | 2017-08-10 | Principia Biopharma, Inc. | Kinase inhibitors |
WO2012158795A1 (en) | 2011-05-17 | 2012-11-22 | Principia Biopharma Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
JP5974084B2 (ja) | 2011-05-17 | 2016-08-23 | プリンシピア バイオファーマ インコーポレイテッド | チロシンキナーゼ阻害剤 |
CN103164756A (zh) * | 2011-12-12 | 2013-06-19 | 苏州艾隆科技有限公司 | 贵重药品的管理方法及其系统 |
CA2882367C (en) | 2012-09-10 | 2021-11-09 | Principia Biopharma Inc. | Pyrazolopyrimidine compounds as kinase inhibitors |
US8957080B2 (en) | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
BR112016018948B1 (pt) | 2014-02-21 | 2023-01-17 | Principia Biopharma Inc | Uso de composto ou sal farmaceuticamente aceitável, ácido sulfônico ou sal de ácido carboxílico de composto, forma amorfa de sal farmaceuticamente aceitável de composto, composição farmacêutica e respectivo uso |
PL3233103T3 (pl) | 2014-12-18 | 2021-04-19 | Principia Biopharma Inc. | Leczenie pęcherzycy |
EP3313839A1 (en) | 2015-06-24 | 2018-05-02 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
KR102515813B1 (ko) | 2016-06-29 | 2023-03-30 | 프린시피아 바이오파마, 인코퍼레이티드 | 2-[3-[4-아미노-3-(2-플루오로-4-페녹시-페닐)피라졸로[3,4-d]피리미딘-1-일]피페리딘-1-카르보닐]-4-메틸-4-[4-(옥세탄-3-일)피페라진-1-일]펜트-2-엔니트릴의 변형 방출 제제 |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1377736A (fr) * | 1962-12-21 | 1964-11-06 | Hoffmann La Roche | Procédé pour la préparation d'acides amino-carboxyliques |
FR1377366A (fr) | 1963-08-19 | 1964-11-06 | Dispositif de protection de sécurité pour appareils électriques | |
KR880007441A (ko) * | 1986-12-11 | 1988-08-27 | 알렌 제이.스피겔 | 스피로-치환된 글루타르아미드 이뇨제 |
WO1991009840A1 (en) | 1989-12-22 | 1991-07-11 | Schering Corporation | Mercaptocycloacyl aminoacid endopeptidase inhibitors |
US5614498A (en) | 1990-06-07 | 1997-03-25 | Banyu Pharmaceutical Co., Ltd. | Endothelin antagonistic substance |
US5011066A (en) * | 1990-07-27 | 1991-04-30 | Motorola, Inc. | Enhanced collapse solder interconnection |
US5239113A (en) | 1991-10-15 | 1993-08-24 | Monsanto Company | Substituted β-amino acid derivatives useful as platelet aggregation inhibitors and intermediates thereof |
EP0561758A3 (en) | 1992-03-18 | 1995-04-05 | Monsanto Co | Method of preparing optically active homo-beta-amino acids |
US5578606A (en) * | 1992-10-30 | 1996-11-26 | G. D. Searle & Co. | α- and β-amino acid hydroxyethylamino sulfonyl urea derivatives useful as retroviral protease inhibitors |
AU684878B2 (en) | 1993-11-24 | 1998-01-08 | Merck & Co., Inc. | Compounds and the use thereof to promote the release of growth hormone(s) |
RU2141760C1 (ru) | 1993-12-12 | 1999-11-27 | Агроджин, Лтд. | Способ защиты растений от грибковой инфекции (варианты) |
US5472830A (en) | 1994-04-18 | 1995-12-05 | Ocg Microelectronic Materials, Inc. | Non-corrosion photoresist stripping composition |
ATE209179T1 (de) | 1996-07-12 | 2001-12-15 | Searle & Co | Asymmetrische synthese von chiralen beta- aminosäuren |
NZ334898A (en) * | 1996-10-23 | 2000-09-29 | Warner Lambert Co | Substituted gamma aminobutyric acids as pharamceutical agents |
US6306909B1 (en) * | 1997-03-12 | 2001-10-23 | Queen's University At Kingston | Anti-epileptogenic agents |
GB2323594A (en) | 1997-03-25 | 1998-09-30 | Victor Martin | 2-amino-alkanoic acid derivatives, 2-amino alcohols and diamines |
US6201023B1 (en) | 1997-06-10 | 2001-03-13 | Agrogene Ltd. | Methods and compositions to protect crops against plant parasitic nematodes |
US6011066A (en) | 1998-02-02 | 2000-01-04 | Veterans General Hospital-Taipei | Method for treating septic shock |
CN1297354A (zh) | 1998-03-16 | 2001-05-30 | 西托维亚公司 | 二肽卡斯帕酶抑制剂及其用途 |
EP1013769A1 (en) | 1998-12-22 | 2000-06-28 | Dsm N.V. | Process for the enzymatic preparation of amino acid derivatives with enhanced optical purity |
FR2791982B1 (fr) | 1999-04-06 | 2002-12-27 | Inst Nat Sante Rech Med | Inhibiteurs de lta4 hydrolase et leurs applications therapeutiques. |
CA2374755C (en) * | 1999-06-10 | 2010-03-30 | Warner-Lambert Company | Mono- and disubstituted 3-propyl gamma-aminobutyric acids |
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 |
JP2004512261A (ja) | 2000-05-17 | 2004-04-22 | メディヴァー ユーケイ リミテッド | 分枝鎖アミノ酸 |
EP1317426B1 (de) | 2000-09-14 | 2005-11-16 | Grünenthal GmbH | Beta-thio-aminosäuren |
DE10048715A1 (de) | 2000-09-30 | 2004-05-19 | Grünenthal GmbH | Verwendung von Aminosäure zur Behandlung von Schmerz |
WO2002073208A2 (en) * | 2001-03-13 | 2002-09-19 | Queen's University At Kingston | Anti-epileptogenic agents |
NI200300043A (es) * | 2002-03-28 | 2003-11-05 | Warner Lambert Co | AMINOACIDOS CON AFINIDAD POR LA PROTEINA a2DELTA. |
GB0219024D0 (en) * | 2002-08-15 | 2002-09-25 | Pfizer Ltd | Synergistic combinations |
CN1228312C (zh) * | 2002-12-27 | 2005-11-23 | 中国科学院化学研究所 | 以酮为原料合成β—氨基酸的方法 |
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