JP2004511560A5 - - Google Patents
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- Publication number
- JP2004511560A5 JP2004511560A5 JP2002536285A JP2002536285A JP2004511560A5 JP 2004511560 A5 JP2004511560 A5 JP 2004511560A5 JP 2002536285 A JP2002536285 A JP 2002536285A JP 2002536285 A JP2002536285 A JP 2002536285A JP 2004511560 A5 JP2004511560 A5 JP 2004511560A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- aryl
- formula
- ome
- 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
- 150000001875 compounds Chemical class 0.000 claims 23
- 238000000034 method Methods 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000002841 Lewis acid Substances 0.000 claims 2
- 125000002015 acyclic group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 150000003949 imides Chemical class 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 150000007517 lewis acids Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 239000012313 reversal agent Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims 1
- RAFFVQBMVYYTQS-UHFFFAOYSA-N 2,4,6-trichlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=C(Cl)C=C1Cl RAFFVQBMVYYTQS-UHFFFAOYSA-N 0.000 claims 1
- OZGSEIVTQLXWRO-UHFFFAOYSA-N 2,4,6-trichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=C(Cl)C=C1Cl OZGSEIVTQLXWRO-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 229910014033 C-OH Inorganic materials 0.000 claims 1
- 229910014570 C—OH Inorganic materials 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000003623 enhancer Substances 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910001853 inorganic hydroxide Inorganic materials 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 239000003791 organic solvent mixture Substances 0.000 claims 1
- 244000045947 parasite Species 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 238000005809 transesterification reaction Methods 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IB2000/001593 WO2002032904A1 (en) | 2000-10-17 | 2000-10-17 | New cephalotaxanes, their method of preparation and their use in treatment of cancers, leukemias, parasites including thus resistant to usual chemotherapeutic agents and as reversal agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004511560A JP2004511560A (ja) | 2004-04-15 |
| JP2004511560A5 true JP2004511560A5 (https=) | 2005-04-14 |
| JP4837233B2 JP4837233B2 (ja) | 2011-12-14 |
Family
ID=11003995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002536285A Expired - Fee Related JP4837233B2 (ja) | 2000-10-17 | 2000-10-17 | 新規なセファロタキサン、それらの製造方法、および通常の化学療法薬に耐性を有する癌、白血病、寄生生物の治療におけるおよび逆転剤としてのそれらの使用 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6579869B1 (https=) |
| EP (1) | EP1328527B1 (https=) |
| JP (1) | JP4837233B2 (https=) |
| CN (1) | CN1303084C (https=) |
| AT (1) | ATE319714T1 (https=) |
| AU (1) | AU7940500A (https=) |
| CA (1) | CA2426103A1 (https=) |
| DE (1) | DE60026557T2 (https=) |
| DK (1) | DK1328527T3 (https=) |
| ES (1) | ES2258024T3 (https=) |
| PT (1) | PT1328527E (https=) |
| WO (1) | WO2002032904A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7285546B2 (en) * | 2000-10-17 | 2007-10-23 | Stragen Pharma S.A. | Cephalotaxanes, their method of preparation and their use in treatment of cancers, leukemias, parasites including those resistant to usual chemotherapeutic agents and as reversal agents |
| US20020128258A1 (en) * | 2001-03-09 | 2002-09-12 | Jean-Pierre Robin | Therapeutical method involving subcutaneous administration of drugs containing cephalotaxine derivatives |
| US20040082565A1 (en) * | 2002-07-17 | 2004-04-29 | Chemgenex Therapeutics, Inc. | Formulations and methods of administration of cephalotaxines including homoharringtonine |
| WO2004009030A2 (en) * | 2002-07-22 | 2004-01-29 | Chemgenex Pharmaceuticals Limited | Angiogenesis inhibition by cephalotaxine alkaloids, derivatives, compositions and uses thereof |
| US8466142B2 (en) | 2008-03-03 | 2013-06-18 | Sloan-Kettering Institute For Cancer Research | Cephalotaxus esters, methods of synthesis, and uses thereof |
| WO2010103405A2 (en) * | 2009-03-11 | 2010-09-16 | Jean-Pierre Robin | Process for preparing cephalotaxine esters |
| CN102304132B (zh) * | 2011-07-12 | 2015-01-28 | 南开大学 | 高效高立体选择性半合成三尖杉酯类生物碱的方法 |
| CN103687859B (zh) * | 2011-08-18 | 2016-08-17 | 杭州本生药业有限公司 | 高三尖杉酯碱的胺化衍生物、及其制备方法和应用 |
| EP2746286A4 (en) * | 2011-08-18 | 2015-01-07 | Hangzhou Bensheng Pharmaceutical Co Ltd | HOMOHARRINGTONIN AMINO DERIVATIVE, PREPARATION METHOD AND APPLICATION THEREOF |
| CN102675327B (zh) * | 2012-03-01 | 2014-12-10 | 南开大学 | 三尖杉酯碱类似物及制备方法和应用 |
| CN104293855A (zh) * | 2014-10-15 | 2015-01-21 | 中国计量学院 | 脐孢木霉菌转化株在提高木霉素产量中的应用 |
| WO2016182850A1 (en) | 2015-05-08 | 2016-11-17 | Albany Molecular Research, Inc. | Methods and intermediates for the preparation of omacetaxine and cephalotaxine derivatives thereof |
| CN106866690B (zh) * | 2015-12-10 | 2019-10-11 | 南开大学 | 三尖杉酯类生物碱、其制备方法和用途 |
| CN109111459B (zh) * | 2017-06-22 | 2021-10-29 | 南华大学 | 含水杨酸三尖杉碱酯衍生物、制造方法及其用途 |
| CN108378049A (zh) * | 2018-05-02 | 2018-08-10 | 孙利嫚 | 一种含有粗榧生物碱和甲氧虫酰肼的农药组合物 |
| WO2024061357A1 (zh) * | 2022-09-22 | 2024-03-28 | 南开大学 | 三尖杉酯碱类衍生物及其药物组合物、制备方法和用途 |
| KR20250160078A (ko) * | 2024-05-03 | 2025-11-11 | 주식회사 아론티어 | 암 연관 섬유아세포 표적용 약학 조성물 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2776292B1 (fr) * | 1998-03-20 | 2004-09-10 | Oncopharm | Cephalotaxanes porteurs de chaine laterale et leur procede de synthese |
-
2000
- 2000-10-13 AU AU7940500A patent/AU7940500A/xx active Pending
- 2000-10-17 EP EP00969759A patent/EP1328527B1/en not_active Expired - Lifetime
- 2000-10-17 DK DK00969759T patent/DK1328527T3/da active
- 2000-10-17 ES ES00969759T patent/ES2258024T3/es not_active Expired - Lifetime
- 2000-10-17 PT PT00969759T patent/PT1328527E/pt unknown
- 2000-10-17 WO PCT/IB2000/001593 patent/WO2002032904A1/en not_active Ceased
- 2000-10-17 AT AT00969759T patent/ATE319714T1/de active
- 2000-10-17 CA CA002426103A patent/CA2426103A1/en not_active Abandoned
- 2000-10-17 DE DE60026557T patent/DE60026557T2/de not_active Expired - Lifetime
- 2000-10-17 CN CNB00820036XA patent/CN1303084C/zh not_active Expired - Fee Related
- 2000-10-17 JP JP2002536285A patent/JP4837233B2/ja not_active Expired - Fee Related
- 2000-11-14 US US09/710,870 patent/US6579869B1/en not_active Expired - Lifetime
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