JP2002539128A5 - - Google Patents
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- Publication number
- JP2002539128A5 JP2002539128A5 JP2000604043A JP2000604043A JP2002539128A5 JP 2002539128 A5 JP2002539128 A5 JP 2002539128A5 JP 2000604043 A JP2000604043 A JP 2000604043A JP 2000604043 A JP2000604043 A JP 2000604043A JP 2002539128 A5 JP2002539128 A5 JP 2002539128A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- iminomethylcamptothecin
- straight
- 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
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- 150000001875 compounds Chemical class 0.000 description 28
- 125000000217 alkyl group Chemical group 0.000 description 16
- -1 2-methylbutoxy Chemical group 0.000 description 9
- 125000003435 aroyl group Chemical group 0.000 description 9
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 229940127093 camptothecin Drugs 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000001204 N-oxides Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- 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 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 0 CC[C@](C(C=C(C)C(C(CN1)=C(C)c2c(*)ccc(C)c2C)=C)=C(CO2)C1=O)(C2=O)O Chemical compound CC[C@](C(C=C(C)C(C(CN1)=C(C)c2c(*)ccc(C)c2C)=C)=C(CO2)C1=O)(C2=O)O 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- KFEUJDWYNGMDBV-LODBTCKLSA-N N-acetyllactosamine Chemical group O[C@@H]1[C@@H](NC(=O)C)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KFEUJDWYNGMDBV-LODBTCKLSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UIVFUQKYVFCEKJ-OPTOVBNMSA-N gimatecan Chemical compound C1=CC=C2C(\C=N\OC(C)(C)C)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UIVFUQKYVFCEKJ-OPTOVBNMSA-N 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99830124.6 | 1999-03-09 | ||
| EP99830124A EP1044977B1 (en) | 1999-03-09 | 1999-03-09 | Camptothecin derivatives having antitumor activity |
| PCT/EP2000/001570 WO2000053607A1 (en) | 1999-03-09 | 2000-03-08 | Camptothecin derivatives having antitumor activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002539128A JP2002539128A (ja) | 2002-11-19 |
| JP2002539128A5 true JP2002539128A5 (enExample) | 2006-06-08 |
| JP4610743B2 JP4610743B2 (ja) | 2011-01-12 |
Family
ID=8243303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000604043A Expired - Fee Related JP4610743B2 (ja) | 1999-03-09 | 2000-03-08 | 抗腫瘍活性を有するカンプトテシン誘導体 |
Country Status (38)
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1140198B1 (en) | 1999-01-13 | 2007-10-31 | Alchemia Oncology Pty Limited | Use of hyaluronan for the manufacture of a medicament for the enhancement of the efficacy of cytotoxic drugs |
| US7105492B2 (en) * | 1999-03-09 | 2006-09-12 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Camptothecin derivatives having antitumor activity |
| FR2794123B1 (fr) * | 1999-05-28 | 2001-07-27 | Aventis Pharma Sa | Preparation de derives de la camptothecine et de la nothapodytine |
| US6352996B1 (en) * | 1999-08-03 | 2002-03-05 | The Stehlin Foundation For Cancer Research | Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs |
| AUPQ879500A0 (en) * | 2000-07-14 | 2000-08-10 | Meditech Research Limited | Hyaluronan as cytotoxic agent, drug presensitizer and chemo-sensitizer in the treatment of disease |
| US9066919B2 (en) * | 2000-07-14 | 2015-06-30 | Alchemia Oncology Pty Limited | Hyaluronan as a chemo-sensitizer in the treatment of cancer |
| US20040029906A1 (en) * | 2001-07-31 | 2004-02-12 | Michael Christman | Inhibitors of dna polymerase sigma |
| MXPA04001828A (es) * | 2001-08-27 | 2005-03-07 | Meditech Res Ltd | Protocolos terapeuticos mejorados. |
| WO2003033525A1 (en) * | 2001-10-12 | 2003-04-24 | Debio Recherche Pharmacuetique S.A. | Amino-substituted camptothecin polymer derivatives and use of the same for the manufacture of a medicament |
| ITRM20020306A1 (it) * | 2002-05-31 | 2003-12-01 | Sigma Tau Ind Farmaceuti | Esteri in posizione 20 di camptotecine. |
| ITRM20020305A1 (it) * | 2002-05-31 | 2003-12-01 | Sigma Tau Ind Farmaceuti | Camptotecine con anello lattonico modificato. |
| FR2852606A1 (fr) * | 2003-03-18 | 2004-09-24 | Inst Nat Sante Rech Med | Moyens pour inhiber simultanement l'expression de plusieurs genes impliques dans une pathologie |
| US20040204435A1 (en) * | 2003-04-09 | 2004-10-14 | Joachim Liehr | Alternating treatment with topoisomerase I and topoisomerase II inhibitors |
| ITRM20030344A1 (it) * | 2003-07-14 | 2005-01-15 | Ist Naz Stud Cura Dei Tumori | 7-n-poliamminoalchil(ossi)imminometilcamptotecine recanti gruppi protettivi. |
| WO2005092302A2 (en) * | 2004-03-26 | 2005-10-06 | Novartis Ag | Use of camptothecin derivates for the treatment of proliferative diseases in a fixed dosing regimen |
| US20070207149A1 (en) | 2004-04-27 | 2007-09-06 | Wellstat Biologics Corporation | Cancer treatment using viruses and camptothecins |
| ITRM20040241A1 (it) * | 2004-05-13 | 2004-08-13 | Ist Naz Stud Cura Dei Tumori | Camptotecine coniugate in posizione 20 con antagonisti delle integrine. |
| ITRM20040242A1 (it) * | 2004-05-13 | 2004-08-13 | Ist Naz Stud Cura Dei Tumori | "7-t-butossiimminometilcamptotecina coniugata in posizione 20 con antagonisti delle integrine. |
| ITRM20040240A1 (it) * | 2004-05-13 | 2004-08-13 | Ist Naz Stud Cura Dei Tumori | Camptotecine coniugate in posizione 7 con antagonisti delle integrine. |
| ITRM20040288A1 (it) * | 2004-06-11 | 2004-09-11 | Sigma Tau Ind Farmaceuti | Uso della 7-t-butossiimminometilcamptotecina per la preparazione di un medicamento per il trattamento delle neoplasie dell'utero. |
| CN100334089C (zh) * | 2004-07-21 | 2007-08-29 | 王洋 | 一种9－硝基喜树碱的生产方法 |
| GT200500310A (es) * | 2004-11-19 | 2006-06-19 | Compuestos organicos | |
| ES2374828T3 (es) * | 2004-12-15 | 2012-02-22 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Combinaciones de agentes terapéuticos para el tratamiento del cáncer. |
| ES2395930T3 (es) | 2004-12-21 | 2013-02-18 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Procedimiento estereoselectivo y formas cristalinas de una camptotecina |
| SA06270147B1 (ar) | 2005-06-09 | 2009-12-22 | نوفارتيس ايه جي | عملية لتخليق 5-(مثيل–1h–إيميدازول–1-يل )–3-(ثلاثي فلـورو مثيل)–بنزامـين |
| CA2612949C (en) | 2005-07-14 | 2015-04-28 | Wellstat Biologics Corporation | Cancer treatment using viruses, fluoropyrimidines and camptothecins |
| CA2616607C (en) * | 2005-07-27 | 2015-06-02 | Alchemia Oncology Pty Limited | Therapeutic protocols using hyaluronan |
| ITRM20050418A1 (it) * | 2005-08-04 | 2007-02-05 | Sigma Tau Ind Farmaceuti | Sistemi terapeutici a rilascio immediato per il migliorato assorbimento orale di 7-[(e)-t-butilossimminometil] camptotecina. |
| US20080213385A1 (en) * | 2005-08-10 | 2008-09-04 | Oskar Kalb | Formulations for 7- (T-Butoxy) Iminomethyl Camptothecin |
| EP1922077A4 (en) * | 2005-09-07 | 2013-03-06 | Alchemia Oncology Pty Ltd | THERAPEUTIC COMPOSITIONS WITH HYALURON AND THERAPEUTIC ANTIBODIES AND TREATMENT PROCEDURES |
| SI1962850T1 (sl) * | 2005-12-21 | 2012-06-29 | Sigma Tau Ind Farmaceuti | Zdravljenje tumorjev, odpornih proti zdravilom |
| EP1989212B1 (en) * | 2006-02-17 | 2013-06-19 | Cascade Prodrug Inc. | Treatment of hyperproliferative diseases with vinca alkaloid n-oxide and analogs |
| EP1998809B1 (en) | 2006-03-30 | 2014-06-25 | Drais Pharmaceuticals, Inc. | Camptothecin-cell penetrating peptide conjugates and pharmaceutical compositions containing the same |
| AU2008210511A1 (en) * | 2007-02-01 | 2008-08-07 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Pharmaceutical composition comprising a campothecin derivative |
| US8853233B2 (en) * | 2007-02-13 | 2014-10-07 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Broad-spectrum anti-cancer treatment based on iminocamptothecin derivatives |
| CA2694389C (en) * | 2007-08-01 | 2016-01-19 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A | Treatment of pediatric tumors |
| EP2096113A1 (en) | 2008-02-05 | 2009-09-02 | SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A. | 9-substituted camptothecin derivatives as antitumor compounds |
| TWI482621B (zh) | 2009-12-23 | 2015-05-01 | Sigma Tau Ind Farmaceuti | 青蒿素基藥物與其他化學治療劑的抗癌組合物 |
| US10517961B2 (en) | 2015-09-25 | 2019-12-31 | ZY Therapeutics, Inc. | Drug formulation based on particulates comprising polysaccharide-vitamin conjugate |
| CN122497675A (zh) * | 2024-06-05 | 2026-07-31 | 荣昌生物制药(烟台)股份有限公司 | 一种喜树碱类化合物及其用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4399276A (en) * | 1981-01-09 | 1983-08-16 | Kabushiki Kaisha Yakult Honsha | 7-Substituted camptothecin derivatives |
| ZA928771B (en) * | 1991-11-15 | 1993-09-08 | Smithkline Beecham Corp | Combination chemotherapy |
| US5614529A (en) * | 1994-09-22 | 1997-03-25 | Research Triangle Institute | Inhibition of plasmodia parasites by camptothecin compounds |
| US5972955A (en) * | 1995-06-06 | 1999-10-26 | Dr. Reddy's Research Foundation | Water soluble C-ring analogues of 20(S)-camptothecin |
| GB9512670D0 (en) * | 1995-06-21 | 1995-08-23 | Sod Conseils Rech Applic | Camptothecin analogues |
| IT1282673B1 (it) * | 1996-02-23 | 1998-03-31 | Ist Naz Stud Cura Dei Tumori | Derivati della camptotecina e loro uso come agenti antitumorali |
| DE69728152T2 (de) * | 1996-08-19 | 2004-08-05 | Bionumerik Pharmaceuticals, Inc., San Antonio | Hoch-lipophile campothecin-derivate |
-
1999
- 1999-03-09 DK DK99830124T patent/DK1044977T3/da active
- 1999-03-09 PT PT99830124T patent/PT1044977E/pt unknown
- 1999-03-09 DE DE69901379T patent/DE69901379T2/de not_active Expired - Lifetime
- 1999-03-09 EP EP99830124A patent/EP1044977B1/en not_active Expired - Lifetime
- 1999-03-09 AT AT99830124T patent/ATE216998T1/de active
- 1999-03-09 SI SI9930010T patent/SI1044977T1/xx unknown
- 1999-03-09 ES ES99830124T patent/ES2175919T3/es not_active Expired - Lifetime
-
2000
- 2000-02-22 US US09/507,928 patent/US6242457B1/en not_active Expired - Lifetime
- 2000-03-07 TW TW089104090A patent/TWI272272B/zh not_active IP Right Cessation
- 2000-03-07 EG EG20000293A patent/EG23999A/xx active
- 2000-03-08 CN CNB008047804A patent/CN1139592C/zh not_active Expired - Fee Related
- 2000-03-08 PL PL355094A patent/PL222208B1/pl unknown
- 2000-03-08 IL IL14495800A patent/IL144958A0/xx unknown
- 2000-03-08 TN TNTNSN00045A patent/TNSN00045A1/fr unknown
- 2000-03-08 TR TR2001/02603T patent/TR200102603T2/xx unknown
- 2000-03-08 MX MXPA01009081A patent/MXPA01009081A/es unknown
- 2000-03-08 CZ CZ2001-3077A patent/CZ304465B6/cs not_active IP Right Cessation
- 2000-03-08 JP JP2000604043A patent/JP4610743B2/ja not_active Expired - Fee Related
- 2000-03-08 CA CA002362760A patent/CA2362760C/en not_active Expired - Fee Related
- 2000-03-08 KR KR1020017011336A patent/KR100702085B1/ko not_active Expired - Fee Related
- 2000-03-08 WO PCT/EP2000/001570 patent/WO2000053607A1/en not_active Ceased
- 2000-03-08 PE PE2000000206A patent/PE20001485A1/es not_active Application Discontinuation
- 2000-03-08 CO CO00016957A patent/CO5180590A1/es active IP Right Grant
- 2000-03-08 NZ NZ513393A patent/NZ513393A/xx not_active IP Right Cessation
- 2000-03-08 EE EEP200100466A patent/EE04679B1/xx not_active IP Right Cessation
- 2000-03-08 HR HR960321A patent/HRP20010667B1/xx not_active IP Right Cessation
- 2000-03-08 ME MEP-40/08A patent/MEP4008A/xx unknown
- 2000-03-08 SK SK1164-2001A patent/SK287561B6/sk not_active IP Right Cessation
- 2000-03-08 RS YUP-643/01A patent/RS50405B/sr unknown
- 2000-03-08 AR ARP000101013A patent/AR022860A1/es not_active Application Discontinuation
- 2000-03-08 BR BRPI0008840-4A patent/BR0008840B1/pt not_active IP Right Cessation
- 2000-03-08 AU AU31604/00A patent/AU774174B2/en not_active Ceased
- 2000-03-08 ME MEP-2008-40A patent/ME00017B/me unknown
- 2000-03-08 EA EA200100954A patent/EA003605B1/ru not_active IP Right Cessation
- 2000-03-08 HU HU0200210A patent/HU229506B1/hu not_active IP Right Cessation
- 2000-12-22 US US09/741,818 patent/US6589939B2/en not_active Expired - Lifetime
-
2001
- 2001-07-31 IS IS6031A patent/IS2003B/is unknown
- 2001-08-10 BG BG105810A patent/BG65032B1/bg unknown
- 2001-08-16 IL IL144958A patent/IL144958A/en not_active IP Right Cessation
- 2001-08-24 NO NO20014128A patent/NO328363B1/no not_active IP Right Cessation
- 2001-09-07 ZA ZA200107408A patent/ZA200107408B/xx unknown
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