CN1817854A - 对α2δ-蛋白质具有亲和性的氨基酸 - Google Patents
对α2δ-蛋白质具有亲和性的氨基酸 Download PDFInfo
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- CN1817854A CN1817854A CNA2006100070283A CN200610007028A CN1817854A CN 1817854 A CN1817854 A CN 1817854A CN A2006100070283 A CNA2006100070283 A CN A2006100070283A CN 200610007028 A CN200610007028 A CN 200610007028A CN 1817854 A CN1817854 A CN 1817854A
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- Prior art keywords
- methyl
- amino
- acid
- amino methyl
- phenyl
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- 150000001413 amino acids Chemical class 0.000 title description 7
- 108090000623 proteins and genes Proteins 0.000 title description 3
- 102000004169 proteins and genes Human genes 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 188
- 150000003839 salts Chemical class 0.000 claims abstract description 72
- 208000002193 Pain Diseases 0.000 claims abstract description 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims description 78
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 70
- 239000000460 chlorine Substances 0.000 claims description 45
- 229910052731 fluorine Inorganic materials 0.000 claims description 36
- 238000002360 preparation method Methods 0.000 claims description 36
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 26
- 201000010099 disease Diseases 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 20
- 208000024891 symptom Diseases 0.000 claims description 20
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 208000004296 neuralgia Diseases 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 208000021722 neuropathic pain Diseases 0.000 claims description 12
- 208000019901 Anxiety disease Diseases 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- SRZDSMJOERDWMK-VXNVDRBHSA-N CCC[C@@H](C)C[C@](C)(C(=O)O)N Chemical compound CCC[C@@H](C)C[C@](C)(C(=O)O)N SRZDSMJOERDWMK-VXNVDRBHSA-N 0.000 claims description 6
- 208000001640 Fibromyalgia Diseases 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 208000000094 Chronic Pain Diseases 0.000 claims description 5
- 208000005298 acute pain Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- WSLCICSXJCXJEN-UHFFFAOYSA-N 2-amino-2,8-dimethylnonanoic acid Chemical compound NC(C(=O)O)(CCCCCC(C)C)C WSLCICSXJCXJEN-UHFFFAOYSA-N 0.000 claims description 4
- 206010060800 Hot flush Diseases 0.000 claims description 4
- 206010065390 Inflammatory pain Diseases 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- VHWJJTKKTVOZNB-UHFFFAOYSA-N 2-amino-2,5-dimethylheptanoic acid Chemical compound CCC(C)CCC(C)(N)C(O)=O VHWJJTKKTVOZNB-UHFFFAOYSA-N 0.000 claims description 3
- BNXWQZYKBIAXNX-UHFFFAOYSA-N 2-amino-2-methyl-3-(1-methylcyclopropyl)propanoic acid Chemical compound NC(C(=O)O)(CC1(CC1)C)C BNXWQZYKBIAXNX-UHFFFAOYSA-N 0.000 claims description 3
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- MIYYJJOPLHOQFD-SMDDNHRTSA-N C[C@@H](CCC1CCCCC1)C[C@](C)(C(=O)O)N Chemical compound C[C@@H](CCC1CCCCC1)C[C@](C)(C(=O)O)N MIYYJJOPLHOQFD-SMDDNHRTSA-N 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- VBDSGELZVDFWLA-GMSGAONNSA-N (2R,4R)-2-amino-5-cyclopropyl-2,4-dimethylpentanoic acid Chemical compound C[C@](C(=O)O)(C[C@@H](CC1CC1)C)N VBDSGELZVDFWLA-GMSGAONNSA-N 0.000 claims description 2
- VBDSGELZVDFWLA-OIBJUYFYSA-N (2R,4S)-2-amino-5-cyclopropyl-2,4-dimethylpentanoic acid Chemical compound C[C@](C(=O)O)(C[C@H](CC1CC1)C)N VBDSGELZVDFWLA-OIBJUYFYSA-N 0.000 claims description 2
- YWAJMILGBXVJTJ-UHFFFAOYSA-N 2-amino-2,4-dimethylhexanoic acid Chemical compound CCC(C)CC(C)(N)C(O)=O YWAJMILGBXVJTJ-UHFFFAOYSA-N 0.000 claims description 2
- CUPGTCAJLARWFC-UHFFFAOYSA-N 2-amino-2,5-dimethylnonanoic acid Chemical compound CC(C(=O)O)(CCC(CCCC)C)N CUPGTCAJLARWFC-UHFFFAOYSA-N 0.000 claims description 2
- WWRRQCYJQMVGIQ-UHFFFAOYSA-N 2-amino-4-ethyl-2,5-dimethylhexanoic acid Chemical compound NC(C(=O)O)(CC(C(C)C)CC)C WWRRQCYJQMVGIQ-UHFFFAOYSA-N 0.000 claims description 2
- FSIIXUWFCWHWNI-UHFFFAOYSA-N 2-amino-4-ethyl-2,8-dimethylnonanoic acid Chemical compound NC(C(=O)O)(CC(CCCC(C)C)CC)C FSIIXUWFCWHWNI-UHFFFAOYSA-N 0.000 claims description 2
- QMSQCBHHTVJEMZ-UHFFFAOYSA-N 2-amino-5-ethyl-2-methylnonanoic acid Chemical compound NC(C(=O)O)(CCC(CCCC)CC)C QMSQCBHHTVJEMZ-UHFFFAOYSA-N 0.000 claims description 2
- OOGXYXOEPLKVST-UHFFFAOYSA-N 2-amino-6-cyclobutyl-2,5-dimethylhexanoic acid Chemical compound NC(C(=O)O)(CCC(CC1CCC1)C)C OOGXYXOEPLKVST-UHFFFAOYSA-N 0.000 claims description 2
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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 |
| BRPI0414798A (pt) | 2003-09-25 | 2006-11-21 | Warner Lambert Co | métodos para usar aminoácidos com afinidade para a proteìna alfa2delta |
| BRPI0414781A (pt) | 2003-09-25 | 2006-11-21 | Warner Lambert Co | aminoácidos com afinidade para a proteìna (alfa)2(delta) |
| RU2335342C2 (ru) * | 2004-03-12 | 2008-10-10 | Уорнер-Ламберт Компани Ллс | C1-симметричные бисфосфиновые лиганды и их применение в асимметрическом синтезе прегабалина |
| US20090247743A1 (en) * | 2004-07-09 | 2009-10-01 | Pfizer Inc | 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 |
| KR20070107147A (ko) * | 2005-03-24 | 2007-11-06 | 파마시아 앤드 업존 캄파니 엘엘씨 | 알파-2-델타 단백질에 친화성을 갖는 광학적으로 순수한베타-아미노산의 제조 |
| WO2007052134A1 (en) * | 2005-11-04 | 2007-05-10 | Pfizer Limited | (2s)-2-aminomethyl-5-ethyl heptanoic acid its pharmaceutical use |
| US20090286875A1 (en) * | 2005-11-17 | 2009-11-19 | Pfizer, Inc. | Isocystene derivatives for the treatment of pain |
| 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 |
| 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 |
| CA2836449C (en) | 2011-05-17 | 2021-04-27 | The Regents Of The University Of California | Kinase inhibitors |
| EA025496B1 (ru) | 2011-05-17 | 2016-12-30 | Принсипиа Биофарма Инк. | Ингибиторы тирозинкиназы |
| US9376438B2 (en) | 2011-05-17 | 2016-06-28 | Principia Biopharma, Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
| 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 |
| ME03455B (me) | 2012-09-10 | 2020-01-20 | Principia Biopharma Inc | Jedinjenja pirazolopirimidina kao inhibitori kinaze |
| US8957080B2 (en) | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| PT3107544T (pt) | 2014-02-21 | 2021-01-05 | Principia Biopharma Inc | Sais e forma sólida de um inibidor de btk |
| US10485797B2 (en) | 2014-12-18 | 2019-11-26 | Principia Biopharma Inc. | Treatment of pemphigus |
| TW201718572A (zh) | 2015-06-24 | 2017-06-01 | 普林斯匹亞生物製藥公司 | 酪胺酸激酶抑制劑 |
| MA45547A (fr) | 2016-06-29 | 2019-05-08 | Principia Biopharma Inc | Formulations à libération modifiée à base de 2-[3-[4-amino-3-(2-fluoro-4-phénoxy-phényl)pyrazolo[3,4-d]pyrimidine-1-yl]pipéridine-1-carbonyl]-4-méthyl-4-[4-(oxétane-3-yl)pipérazine-1-yl]pent-2-ènenitrile |
| TWI877239B (zh) | 2019-10-14 | 2025-03-21 | 美商普林斯匹亞生物製藥公司 | 藉由投予(R)-2-[3-[4-胺基-3-(2-氟-4-苯氧基-苯基)吡唑并[3,4-d]嘧啶-1-基]哌啶-1-羰基]-4-甲基-4-[4-(氧呾-3-基)哌-1-基]戊-2-烯腈來治療免疫血小板減少症之方法 |
| JP2023511105A (ja) | 2020-01-22 | 2023-03-16 | プリンシピア バイオファーマ インコーポレイテッド | 2-[3-[4-アミノ-3-(2-フルオロ-4-フェノキシ-フェニル)-1h-ピラゾロ[3,4-d]ピリミジン-1-イル]ピペリジン-1-カルボニル]-4-メチル-4-[4-(オキセタン-3-イル)ピペラジン-1-イル]ペンタ-2-エンニトリルの結晶形態 |
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| 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 | |
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| AU7168091A (en) | 1989-12-22 | 1991-07-24 | Schering Corporation | Mercaptocycloacyl aminoacid endopeptidase inhibitors |
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| 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 |
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