JP2010518120A5 - - Google Patents
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- JP2010518120A5 JP2010518120A5 JP2009549259A JP2009549259A JP2010518120A5 JP 2010518120 A5 JP2010518120 A5 JP 2010518120A5 JP 2009549259 A JP2009549259 A JP 2009549259A JP 2009549259 A JP2009549259 A JP 2009549259A JP 2010518120 A5 JP2010518120 A5 JP 2010518120A5
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- Prior art keywords
- pharmaceutical composition
- compound
- composition according
- cancer
- refractory
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 23
- 208000016691 refractory malignant neoplasm Diseases 0.000 claims 16
- 206010070308 Refractory cancer Diseases 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 229920000642 polymer Polymers 0.000 claims 5
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims 5
- FJHBVJOVLFPMQE-QFIPXVFZSA-N 7-Ethyl-10-Hydroxy-Camptothecin Chemical compound C1=C(O)C=C2C(CC)=C(CN3C(C4=C([C@@](C(=O)OC4)(O)CC)C=C33)=O)C3=NC2=C1 FJHBVJOVLFPMQE-QFIPXVFZSA-N 0.000 claims 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims 4
- 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 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 4
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 3
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 3
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims 3
- 206010009944 Colon cancer Diseases 0.000 claims 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 229940127093 camptothecin Drugs 0.000 claims 3
- 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 claims 3
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 3
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 2
- OYIFNHCXNCRBQI-UHFFFAOYSA-N 2-aminoadipic acid Chemical group OC(=O)C(N)CCCC(O)=O OYIFNHCXNCRBQI-UHFFFAOYSA-N 0.000 claims 2
- RDFMDVXONNIGBC-UHFFFAOYSA-N 2-aminoheptanoic acid Chemical compound CCCCCC(N)C(O)=O RDFMDVXONNIGBC-UHFFFAOYSA-N 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- KSPIYJQBLVDRRI-UHFFFAOYSA-N N-methylisoleucine Chemical compound CCC(C)C(NC)C(O)=O KSPIYJQBLVDRRI-UHFFFAOYSA-N 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 108010077895 Sarcosine Proteins 0.000 claims 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 claims 2
- 150000003862 amino acid derivatives Chemical class 0.000 claims 2
- -1 amino, substituted amino, azide Chemical class 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 2
- 206010017758 gastric cancer Diseases 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- BJBUEDPLEOHJGE-UHFFFAOYSA-N (2R,3S)-3-Hydroxy-2-pyrolidinecarboxylic acid Natural products OC1CCNC1C(O)=O BJBUEDPLEOHJGE-UHFFFAOYSA-N 0.000 claims 1
- VEVRNHHLCPGNDU-MUGJNUQGSA-N (2s)-2-amino-5-[1-[(5s)-5-amino-5-carboxypentyl]-3,5-bis[(3s)-3-amino-3-carboxypropyl]pyridin-1-ium-4-yl]pentanoate Chemical compound OC(=O)[C@@H](N)CCCC[N+]1=CC(CC[C@H](N)C(O)=O)=C(CCC[C@H](N)C([O-])=O)C(CC[C@H](N)C(O)=O)=C1 VEVRNHHLCPGNDU-MUGJNUQGSA-N 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- JHTPBGFVWWSHDL-UHFFFAOYSA-N 1,4-dichloro-2-isothiocyanatobenzene Chemical compound ClC1=CC=C(Cl)C(N=C=S)=C1 JHTPBGFVWWSHDL-UHFFFAOYSA-N 0.000 claims 1
- HAWJUUUDZFZUKG-UHFFFAOYSA-N 2,2-diaminoheptanedioic acid Chemical compound OC(=O)C(N)(N)CCCCC(O)=O HAWJUUUDZFZUKG-UHFFFAOYSA-N 0.000 claims 1
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 claims 1
- XABCFXXGZPWJQP-UHFFFAOYSA-N 3-aminoadipic acid Chemical compound OC(=O)CC(N)CCC(O)=O XABCFXXGZPWJQP-UHFFFAOYSA-N 0.000 claims 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 101001046870 Homo sapiens Hypoxia-inducible factor 1-alpha Proteins 0.000 claims 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims 1
- 102100022875 Hypoxia-inducible factor 1-alpha Human genes 0.000 claims 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims 1
- JUQLUIFNNFIIKC-YFKPBYRVSA-N L-2-aminopimelic acid Chemical compound OC(=O)[C@@H](N)CCCCC(O)=O JUQLUIFNNFIIKC-YFKPBYRVSA-N 0.000 claims 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- AGPKZVBTJJNPAG-UHNVWZDZSA-N L-allo-Isoleucine Chemical compound CC[C@@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-UHNVWZDZSA-N 0.000 claims 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 1
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 claims 1
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 1
- OLNLSTNFRUFTLM-UHFFFAOYSA-N N-ethylasparagine Chemical compound CCNC(C(O)=O)CC(N)=O OLNLSTNFRUFTLM-UHFFFAOYSA-N 0.000 claims 1
- YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 claims 1
- 108010065338 N-ethylglycine Proteins 0.000 claims 1
- AKCRVYNORCOYQT-YFKPBYRVSA-N N-methyl-L-valine Chemical compound CN[C@@H](C(C)C)C(O)=O AKCRVYNORCOYQT-YFKPBYRVSA-N 0.000 claims 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 229940024606 amino acid Drugs 0.000 claims 1
- 235000001014 amino acid Nutrition 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 229960002684 aminocaproic acid Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 229940000635 beta-alanine Drugs 0.000 claims 1
- 230000001588 bifunctional effect Effects 0.000 claims 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000004405 heteroalkoxy group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229960002591 hydroxyproline Drugs 0.000 claims 1
- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 208000037819 metastatic cancer Diseases 0.000 claims 1
- 208000011575 metastatic malignant neoplasm Diseases 0.000 claims 1
- 229930182817 methionine Natural products 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- KITHNHJPIHPBQH-UHFFFAOYSA-N nitro(nitrosilyloxy)silane Chemical compound [N+](=O)([O-])[SiH2]O[SiH2][N+](=O)[O-] KITHNHJPIHPBQH-UHFFFAOYSA-N 0.000 claims 1
- 229960003104 ornithine Drugs 0.000 claims 1
- 229940043230 sarcosine Drugs 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- BJBUEDPLEOHJGE-IMJSIDKUSA-N trans-3-hydroxy-L-proline Chemical compound O[C@H]1CC[NH2+][C@@H]1C([O-])=O BJBUEDPLEOHJGE-IMJSIDKUSA-N 0.000 claims 1
- 230000003442 weekly effect Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90059207P | 2007-02-09 | 2007-02-09 | |
| PCT/US2008/053438 WO2008098178A2 (en) | 2007-02-09 | 2008-02-08 | Treatment of resistant or refractory cancers with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010518120A JP2010518120A (ja) | 2010-05-27 |
| JP2010518120A5 true JP2010518120A5 (enExample) | 2012-04-12 |
Family
ID=39682430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009549259A Pending JP2010518120A (ja) | 2007-02-09 | 2008-02-08 | ７−エチル−１０−ヒドロキシカンプトテシンのマルチアームポリマー複合体を用いた抵抗性または難治性の癌の治療方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7928095B2 (enExample) |
| EP (1) | EP2109448B1 (enExample) |
| JP (1) | JP2010518120A (enExample) |
| KR (1) | KR20090108082A (enExample) |
| CN (1) | CN101605539B (enExample) |
| AU (1) | AU2008213576B2 (enExample) |
| BR (1) | BRPI0807232A2 (enExample) |
| CA (1) | CA2677798A1 (enExample) |
| IL (1) | IL200100A0 (enExample) |
| MX (1) | MX2009008549A (enExample) |
| RU (1) | RU2009133793A (enExample) |
| TW (1) | TW200902066A (enExample) |
| WO (1) | WO2008098178A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7671067B2 (en) * | 2006-02-09 | 2010-03-02 | Enzon Pharmaceuticals, Inc. | Treatment of non-hodgkin's lymphomas with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamtothecin |
| US7462627B2 (en) * | 2006-02-09 | 2008-12-09 | Enzon Pharmaceuticals, Inc. | Multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin for treatment of breast, colorectal, pancreatic, ovarian and lung cancers |
| EP2109448B1 (en) | 2007-02-09 | 2013-09-11 | Enzon Pharmaceuticals, Inc. | Treatment of resistant or refractory cancers with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin |
| JP2011520983A (ja) * | 2008-05-23 | 2011-07-21 | エンゾン ファーマシューティカルズ，インコーポレーテッド | オリゴヌクレオチドの送達のための細胞内遊離可能ジスルフィドリンカーを含有するポリマーシステム |
| WO2010025337A1 (en) * | 2008-08-29 | 2010-03-04 | Enzon Pharmaceuticals, Inc. | Method of treating ras associated cancer |
| RS59607B1 (sr) * | 2008-09-23 | 2020-01-31 | Nektar Therapeutics | Metod metronomskog doziranja kamptotecinskih prolekova (npr. peg-irinotekan) |
| JP2012506380A (ja) * | 2008-10-21 | 2012-03-15 | エンゾン ファーマシューティカルズ，インコーポレーテッド | ７−エチル−１０−ヒドロキシカンプトテシンのマルチアーム型ポリマーコンジュゲートによる神経芽腫の治療 |
| CA2758263A1 (en) * | 2009-04-17 | 2010-10-21 | Enzon Pharmaceuticals, Inc. | Methods for inhibiting angiogenesis with multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin |
| BR112012001395A2 (pt) * | 2009-07-22 | 2019-09-24 | Enzon Pharmaceuticals Inc | metodo para tratar um câncer her2 positivo em um mamifero metodo para aumentar os efetivos de antagonistas do receptor her2 em um mamifero apresentando um cancêr her2 positivo metodo para inibir o crescimento ou proliferação de células her2 positivas em um mamifero |
| CN104650342B (zh) * | 2013-11-18 | 2018-07-10 | 江苏豪森药业集团有限公司 | 多支链聚合药物前体及其应用 |
| CN103772696B (zh) * | 2014-01-06 | 2015-12-02 | 济南大学 | 一种羟基喜树碱的聚甘油脂肪酸酯衍生物 |
| CN110448533B (zh) * | 2014-12-05 | 2022-03-29 | 天津键凯科技有限公司 | 一种聚乙二醇修饰的喜树碱类衍生物的药物组合物及其制备方法 |
| CN108727584B (zh) * | 2017-04-21 | 2021-01-05 | 博瑞生物医药（苏州）股份有限公司 | 抗癌偶联物 |
| CN107670050B (zh) * | 2017-08-30 | 2019-06-07 | 重庆阿普格雷生物科技有限公司 | 基于pki-587的抗癌中间体和聚乙二醇偶联抗癌药物、及其制备方法和应用 |
| CN115052632B (zh) * | 2020-01-15 | 2025-01-14 | 北京海步医药科技有限公司 | 靶向多肽-药物缀合物及其用途 |
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-
2008
- 2008-02-08 EP EP08729405.4A patent/EP2109448B1/en not_active Not-in-force
- 2008-02-08 WO PCT/US2008/053438 patent/WO2008098178A2/en not_active Ceased
- 2008-02-08 CN CN2008800046084A patent/CN101605539B/zh not_active Expired - Fee Related
- 2008-02-08 KR KR1020097016812A patent/KR20090108082A/ko not_active Ceased
- 2008-02-08 RU RU2009133793/15A patent/RU2009133793A/ru unknown
- 2008-02-08 AU AU2008213576A patent/AU2008213576B2/en not_active Ceased
- 2008-02-08 MX MX2009008549A patent/MX2009008549A/es unknown
- 2008-02-08 BR BRPI0807232-9A patent/BRPI0807232A2/pt not_active IP Right Cessation
- 2008-02-08 JP JP2009549259A patent/JP2010518120A/ja active Pending
- 2008-02-08 US US12/028,378 patent/US7928095B2/en not_active Expired - Fee Related
- 2008-02-08 CA CA002677798A patent/CA2677798A1/en not_active Abandoned
- 2008-02-12 TW TW097104779A patent/TW200902066A/zh unknown
-
2009
- 2009-07-28 IL IL200100A patent/IL200100A0/en unknown
-
2011
- 2011-04-18 US US13/088,825 patent/US20110195990A1/en not_active Abandoned
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