CA2703054C - Hydrated crystalline esters of camptothecin for the treatment of cancer - Google Patents
Hydrated crystalline esters of camptothecin for the treatment of cancer Download PDFInfo
- Publication number
- CA2703054C CA2703054C CA2703054A CA2703054A CA2703054C CA 2703054 C CA2703054 C CA 2703054C CA 2703054 A CA2703054 A CA 2703054A CA 2703054 A CA2703054 A CA 2703054A CA 2703054 C CA2703054 C CA 2703054C
- Authority
- CA
- Canada
- Prior art keywords
- cancer
- crystalline
- camptothecin
- hydrate
- crystalline camptothecin
- 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.)
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- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 title claims abstract description 98
- 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 title claims abstract description 96
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- 239000012453 solvate Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 231100000211 teratogenicity Toxicity 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 239000002691 unilamellar liposome Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/923,727 US7572803B2 (en) | 2007-10-25 | 2007-10-25 | Hydrated crystalline esters of camptothecin |
| US11/923,727 | 2007-10-25 | ||
| PCT/US2008/081047 WO2009055633A1 (en) | 2007-10-25 | 2008-10-24 | Hydrated crystalline esters of camptothecin for the treatment of cancer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2703054A1 CA2703054A1 (en) | 2009-04-30 |
| CA2703054C true CA2703054C (en) | 2017-08-22 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2703054A Active CA2703054C (en) | 2007-10-25 | 2008-10-24 | Hydrated crystalline esters of camptothecin for the treatment of cancer |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7572803B2 (OSRAM) |
| EP (1) | EP2205605B1 (OSRAM) |
| JP (1) | JP5487111B2 (OSRAM) |
| KR (1) | KR20100082358A (OSRAM) |
| CN (1) | CN101730701B (OSRAM) |
| BR (1) | BRPI0816584A2 (OSRAM) |
| CA (1) | CA2703054C (OSRAM) |
| ES (1) | ES2396222T3 (OSRAM) |
| MX (1) | MX2010004332A (OSRAM) |
| RU (1) | RU2483071C2 (OSRAM) |
| WO (1) | WO2009055633A1 (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130121921A1 (en) | 2011-11-11 | 2013-05-16 | The Christus Stehlin Foundation For Cancer Research | Rodent Therapeutic Model And Methods |
| US9387257B2 (en) * | 2014-01-17 | 2016-07-12 | Academia Sinica | Lung cancer specific peptides for targeted drug delivery and molecular imaging |
| US9675609B2 (en) | 2015-11-11 | 2017-06-13 | Cao Pharmaceuticals Inc. | Nano- and micro-sized particles of 20-camptothecin or derivative thereof and pharmaceutical compositions containing same, and treatment of cancers therewith |
| US20220395497A1 (en) * | 2019-11-20 | 2022-12-15 | Vivacitas Oncology, Inc. | Cancer Treatment Using Camptothecin Derivatives |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5552154A (en) * | 1989-11-06 | 1996-09-03 | The Stehlin Foundation For Cancer Research | Method for treating cancer with water-insoluble s-camptothecin of the closed lactone ring form and derivatives thereof |
| US6080751A (en) * | 1992-01-14 | 2000-06-27 | The Stehlin Foundation For Cancer Research | Method for treating pancreatic cancer in humans with water-insoluble S-camptothecin of the closed lactone ring form and derivatives thereof |
| US5527913A (en) * | 1993-02-25 | 1996-06-18 | The Stehlin Foundation For Cancer Research | Methods for purifying camptothecin compounds |
| US5352789A (en) * | 1993-02-25 | 1994-10-04 | The Stehlin Foundation For Cancer Research | Methods for purifying camptothecin compounds |
| US5731316A (en) | 1996-01-30 | 1998-03-24 | The Stehlin Foundation For Cancer Research | Derivatives of camptothecin and methods of treating cancer using these derivatives |
| US6407118B1 (en) * | 1996-01-30 | 2002-06-18 | The Stehlin Foundation For Cancer Research | Derivatives of camptothecin and methods of treating cancer using these derivatives |
| US6096336A (en) * | 1996-01-30 | 2000-08-01 | The Stehlin Foundation For Cancer Research | Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs |
| US5922877A (en) * | 1997-08-05 | 1999-07-13 | The Stehlin Foundation For Cancer Research | Methods of preparing and purifying 9-nitro-20-camptothecin |
| USRE38408E1 (en) * | 1997-08-05 | 2004-01-27 | The Stehlin Foundation For Cancer Research | Methods of preparing and purifying 9-nitro-20-camptothecin |
| US6228855B1 (en) * | 1999-08-03 | 2001-05-08 | The Stehlin Foundation For Cancer Research | Aromatic esters of camptothecins and methods to treat cancers |
| 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 |
| US6699875B2 (en) * | 2002-05-06 | 2004-03-02 | The Stehlin Foundation For Cancer Research | Cascade esters of camptothecins and methods of treating cancer using these compounds |
| US6703399B2 (en) * | 2002-05-06 | 2004-03-09 | The Stehlin Foundation For Cancer Research | Halo-alkyl esters of camptothecins and methods of treating cancer using these compounds |
| KR101095382B1 (ko) * | 2003-02-25 | 2011-12-16 | 가부시키가이샤 야쿠르트 혼샤 | 이리노테칸 염산염의 결정다형의 제조방법 |
| TWI333492B (en) * | 2003-11-12 | 2010-11-21 | Smithkline Beecham Cork Ltd | Crystalline topotecan hydrochloride product and preparation thereof |
| WO2007035709A2 (en) * | 2005-09-20 | 2007-03-29 | Scinopharm Singapore Pte, Ltd. | Novel crystal forms of irinotecan hydrochloride |
-
2007
- 2007-10-25 US US11/923,727 patent/US7572803B2/en active Active
-
2008
- 2008-10-24 EP EP08841603A patent/EP2205605B1/en not_active Not-in-force
- 2008-10-24 CA CA2703054A patent/CA2703054C/en active Active
- 2008-10-24 BR BRPI0816584-0A2A patent/BRPI0816584A2/pt not_active IP Right Cessation
- 2008-10-24 KR KR1020107011223A patent/KR20100082358A/ko not_active Ceased
- 2008-10-24 CN CN200880013536XA patent/CN101730701B/zh not_active Expired - Fee Related
- 2008-10-24 MX MX2010004332A patent/MX2010004332A/es active IP Right Grant
- 2008-10-24 JP JP2010531264A patent/JP5487111B2/ja not_active Expired - Fee Related
- 2008-10-24 WO PCT/US2008/081047 patent/WO2009055633A1/en not_active Ceased
- 2008-10-24 RU RU2010120810/04A patent/RU2483071C2/ru not_active IP Right Cessation
- 2008-10-24 ES ES08841603T patent/ES2396222T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101730701B (zh) | 2013-05-29 |
| ES2396222T3 (es) | 2013-02-20 |
| US20090111845A1 (en) | 2009-04-30 |
| RU2483071C2 (ru) | 2013-05-27 |
| RU2010120810A (ru) | 2011-11-27 |
| BRPI0816584A2 (pt) | 2015-03-03 |
| CN101730701A (zh) | 2010-06-09 |
| KR20100082358A (ko) | 2010-07-16 |
| MX2010004332A (es) | 2010-05-20 |
| EP2205605A1 (en) | 2010-07-14 |
| CA2703054A1 (en) | 2009-04-30 |
| JP5487111B2 (ja) | 2014-05-07 |
| JP2011500841A (ja) | 2011-01-06 |
| WO2009055633A1 (en) | 2009-04-30 |
| EP2205605B1 (en) | 2012-11-21 |
| US7572803B2 (en) | 2009-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20131024 |