JP2008538743A5 - - Google Patents
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- Publication number
- JP2008538743A5 JP2008538743A5 JP2008501969A JP2008501969A JP2008538743A5 JP 2008538743 A5 JP2008538743 A5 JP 2008538743A5 JP 2008501969 A JP2008501969 A JP 2008501969A JP 2008501969 A JP2008501969 A JP 2008501969A JP 2008538743 A5 JP2008538743 A5 JP 2008538743A5
- Authority
- JP
- Japan
- Prior art keywords
- pteroic acid
- derivative
- pteroic
- group
- following formula
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 28
- JOAQINSXLLMRCV-UHFFFAOYSA-N 4-{[(2-amino-4-hydroxypteridin-6-yl)methyl]amino}benzoic acid Chemical compound C1=NC2=NC(N)=NC(O)=C2N=C1CNC1=CC=C(C(O)=O)C=C1 JOAQINSXLLMRCV-UHFFFAOYSA-N 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 229910019142 PO4 Inorganic materials 0.000 claims 5
- 229920002678 cellulose Polymers 0.000 claims 5
- 239000001913 cellulose Substances 0.000 claims 5
- 238000004255 ion exchange chromatography Methods 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 5
- 239000010452 phosphate Substances 0.000 claims 5
- 229920005654 Sephadex Polymers 0.000 claims 4
- 239000012507 Sephadex™ Substances 0.000 claims 4
- 150000001720 carbohydrates Chemical class 0.000 claims 4
- 239000002244 precipitate Substances 0.000 claims 4
- 230000001376 precipitating effect Effects 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims 3
- 239000003957 anion exchange resin Substances 0.000 claims 3
- 229960000304 folic acid Drugs 0.000 claims 3
- 235000019152 folic acid Nutrition 0.000 claims 3
- 239000011724 folic acid Substances 0.000 claims 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 claims 2
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims 2
- 150000002224 folic acids Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- 229920000856 Amylose Polymers 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000005571 anion exchange chromatography Methods 0.000 claims 1
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 230000028993 immune response Effects 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 230000001717 pathogenic effect Effects 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 C*(CCC(O*)=O)C(C(O*)=O)N Chemical compound C*(CCC(O*)=O)C(C(O*)=O)N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66227705P | 2005-03-16 | 2005-03-16 | |
| US60/662,277 | 2005-03-16 | ||
| PCT/US2006/009153 WO2006101845A2 (en) | 2005-03-16 | 2006-03-14 | Synthesis and purification of pteroic acid and conjugates thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008538743A JP2008538743A (ja) | 2008-11-06 |
| JP2008538743A5 true JP2008538743A5 (https=) | 2009-04-30 |
| JP5289935B2 JP5289935B2 (ja) | 2013-09-11 |
Family
ID=36699050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008501969A Expired - Fee Related JP5289935B2 (ja) | 2005-03-16 | 2006-03-14 | プテロイン酸およびその結合体の合成と精製 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8044200B2 (https=) |
| EP (1) | EP1863816B1 (https=) |
| JP (1) | JP5289935B2 (https=) |
| CN (1) | CN101175757B (https=) |
| WO (1) | WO2006101845A2 (https=) |
Families Citing this family (39)
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| ATE427948T1 (de) | 2001-04-24 | 2009-04-15 | Purdue Research Foundation | Folat-mimetika und deren folatrezeptorbindende konjugate |
| CN101979095A (zh) | 2001-05-02 | 2011-02-23 | 普渡研究基金会 | 巨噬细胞介导的疾病的治疗和诊断 |
| US8043603B2 (en) | 2002-02-07 | 2011-10-25 | Endocyte, Inc. | Folate targeted enhanced tumor and folate receptor positive tissue optical imaging technology |
| US8043602B2 (en) | 2002-02-07 | 2011-10-25 | Endocyte, Inc. | Folate targeted enhanced tumor and folate receptor positive tissue optical imaging technology |
| WO2004069159A2 (en) | 2003-01-27 | 2004-08-19 | Endocyte, Inc. | Vitamin receptor binding drug delivery conjugates |
| WO2004110250A2 (en) | 2003-05-30 | 2004-12-23 | Purdue Research Foundation | Diagnostic method for atherosclerosis |
| CN101098854B (zh) * | 2004-07-23 | 2012-12-05 | 恩多塞特公司 | 二价连接体及其轭合物 |
| CN101175757B (zh) | 2005-03-16 | 2012-11-14 | 恩多塞特公司 | 蝶酸及其缀合物的合成和纯化 |
| EP1904183B1 (en) | 2005-07-05 | 2014-10-15 | Purdue Research Foundation | Pharmaceutical composition for the treatment of osteoarthritis |
| EP2382995A3 (en) * | 2005-08-19 | 2013-09-25 | Endocyte, Inc. | Ligand conjugates of Vinca alkaloids, analogs and derivatives |
| BRPI0615354A2 (pt) * | 2005-08-19 | 2011-05-17 | Endocyte, Inc. | conjugado de liberação de fármaco de ligação de receptor, composição farmacêutica que o compreende, bem como seu uso |
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| JP2010509570A (ja) | 2006-11-03 | 2010-03-25 | パーデュー・リサーチ・ファウンデーション | エクスビボフローサイトメトリーの方法および装置 |
| US8586595B2 (en) | 2007-02-07 | 2013-11-19 | Purdue Research Foundation | Positron emission tomography imaging method |
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| US9877965B2 (en) | 2007-06-25 | 2018-01-30 | Endocyte, Inc. | Vitamin receptor drug delivery conjugates for treating inflammation |
| CN101784565B (zh) | 2007-06-25 | 2014-12-10 | 恩多塞特公司 | 含有亲水性间隔区接头的共轭物 |
| CN101909441B (zh) | 2007-10-25 | 2015-05-13 | 恩多塞特公司 | 微管蛋白抑制剂及其制备方法 |
| ES3029483T3 (en) | 2008-09-17 | 2025-06-24 | Endocyte Inc | Folate receptor binding conjugates of antifolates |
| BR112012002064A2 (pt) * | 2009-07-31 | 2017-05-09 | Endocyte Inc | método para determinar se ec145 é indicado para o tratamento de um paciente com um tumor ovariano ou um tumor de pulmão; método para prever uma resposta de um tumor ovariano ou um tumor de pulmão de um paciente a terapia com ec145; método de tratamento de câncer ovariano resistente à platina em um paciente necessitando dele; uso de ec145 em combinação com doxorrubicina lipossômica peguilada; uso de ec145 para a fabricação de um medicamento; método para obter um benefício clínico comparado a tratamento com uma quantidade terapêutica de doxorrubicina lipossômica peguilada no tratamento de câncer ovariano resistente à platina em um paciente necessitando dele; método para selecionar um paciente para tratamento; composição farmacêutica; unidade de dosagem, método para determinar se um paciente com um tumor tem receptores de folato funcionalmente ativos presentes no tumor do paciente; método de tratamento de um tumor epitelial expressando receptor de folato em um paciente necessitando dele; e; método para obter um benefício clínico no tratamento de um tumor epitelial expressando receptor de folato em um paciente necessitando dele |
| EP2476414B1 (en) * | 2009-09-07 | 2015-03-04 | NIPRO Patch Co., Ltd. | Transdermally absorbable preparation |
| US10080805B2 (en) | 2012-02-24 | 2018-09-25 | Purdue Research Foundation | Cholecystokinin B receptor targeting for imaging and therapy |
| US20140080175A1 (en) | 2012-03-29 | 2014-03-20 | Endocyte, Inc. | Processes for preparing tubulysin derivatives and conjugates thereof |
| BR112015008365A2 (pt) | 2012-10-16 | 2017-07-04 | Endocyte Inc | composto da fórmula b-l(d)x, ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, uso de um composto, composição de forma de dosagem unitária ou dose unitária, composição para tratar um câncer em um paciente, e método para tratar um câncer em um paciente |
| WO2014149069A1 (en) * | 2013-03-15 | 2014-09-25 | Purdue Research Foundation | Synthesis and composition of amino acid linking groups conjugated to compounds used for the targeted imaging of tumors |
| WO2015077303A1 (en) | 2013-11-19 | 2015-05-28 | Purdue Research Foundation | Patient selection method for inflammation |
| US10239891B2 (en) * | 2017-05-15 | 2019-03-26 | Indicator Systems International, Inc. | Compositions to detect remnant cancer cells |
| WO2018026965A1 (en) | 2016-08-02 | 2018-02-08 | Isi Life Sciences, Inc. | Compositions and methods for detecting cancer cells in a tissue sample |
| US20180036312A1 (en) * | 2016-08-02 | 2018-02-08 | ISI Life Sciences Inc. | Novel Scaffolds for Intracellular Compound Delivery for the Detection of Cancer Cells |
| CN106420394B (zh) * | 2016-10-21 | 2019-05-10 | 江南大学 | 一种增强叶酸光稳定性的方法 |
| US10753942B2 (en) | 2017-05-15 | 2020-08-25 | Indicator Systems International, Inc. | Methods to detect remnant cancer cells |
| CN109734717B (zh) * | 2019-01-24 | 2022-03-22 | 苏州华健瑞达医药技术有限公司 | 蝶酸新晶型及其制备方法 |
| EP4274619A4 (en) * | 2021-01-08 | 2025-09-24 | Lycia Therapeutics Inc | BIFUNCTIONAL FOLATE RECEPTOR-BINDING COMPOUNDS |
| US20250127913A1 (en) * | 2021-06-24 | 2025-04-24 | Lycia Therapeutics, Inc. | Bifunctional folate receptor binding compounds |
| CN116218513A (zh) * | 2023-03-03 | 2023-06-06 | 杭州谱康医学科技有限公司 | Fitc标记的荧光微球、制备方法及应用 |
| CN116621838A (zh) * | 2023-04-17 | 2023-08-22 | 武汉翱飞科技有限公司 | 一种蝶酸活性酯及其合成方法 |
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2006
- 2006-03-14 CN CN2006800162870A patent/CN101175757B/zh not_active Expired - Fee Related
- 2006-03-14 US US11/908,695 patent/US8044200B2/en not_active Expired - Fee Related
- 2006-03-14 EP EP06738235.8A patent/EP1863816B1/en not_active Expired - Lifetime
- 2006-03-14 JP JP2008501969A patent/JP5289935B2/ja not_active Expired - Fee Related
- 2006-03-14 WO PCT/US2006/009153 patent/WO2006101845A2/en not_active Ceased
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