JP2009526076A5 - - Google Patents
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- Publication number
- JP2009526076A5 JP2009526076A5 JP2008554430A JP2008554430A JP2009526076A5 JP 2009526076 A5 JP2009526076 A5 JP 2009526076A5 JP 2008554430 A JP2008554430 A JP 2008554430A JP 2008554430 A JP2008554430 A JP 2008554430A JP 2009526076 A5 JP2009526076 A5 JP 2009526076A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- substituted
- group
- cycloalkyl
- 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 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine zwitterion Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 6
- UCMIRNVEIXFBKS-UHFFFAOYSA-N β-Alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 4
- 108010077895 Sarcosine Proteins 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 235000001014 amino acid Nutrition 0.000 claims description 3
- 150000003862 amino acid derivatives Chemical class 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- HAWJUUUDZFZUKG-UHFFFAOYSA-N 2,2-diaminoheptanedioic acid Chemical compound OC(=O)C(N)(N)CCCCC(O)=O HAWJUUUDZFZUKG-UHFFFAOYSA-N 0.000 claims description 2
- PECYZEOJVXMISF-REOHCLBHSA-N 2,3-Diaminopropionic acid Chemical compound [NH3+]C[C@H](N)C([O-])=O PECYZEOJVXMISF-REOHCLBHSA-N 0.000 claims description 2
- QCHPKSFMDHPSNR-UHFFFAOYSA-N 3-Aminoisobutyric acid Chemical compound NCC(C)C(O)=O QCHPKSFMDHPSNR-UHFFFAOYSA-N 0.000 claims description 2
- XABCFXXGZPWJQP-UHFFFAOYSA-N 3-aminoadipic acid Chemical compound OC(=O)CC(N)CCC(O)=O XABCFXXGZPWJQP-UHFFFAOYSA-N 0.000 claims description 2
- BJBUEDPLEOHJGE-BKLSDQPFSA-N 3-hydroxy-L-proline Chemical compound OC1CCN[C@@H]1C(O)=O BJBUEDPLEOHJGE-BKLSDQPFSA-N 0.000 claims description 2
- 229940000687 6-Aminocaproic Acid Drugs 0.000 claims description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N Aminocaproic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 2
- VEVRNHHLCPGNDU-MUGJNUQGSA-O Desmosine 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-O 0.000 claims description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N GABA Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- 229960002591 Hydroxyproline Drugs 0.000 claims description 2
- OGNSCSPNOLGXSM-VKHMYHEASA-N L-2,4-diaminobutyric acid Chemical compound NCC[C@H](N)C(O)=O OGNSCSPNOLGXSM-VKHMYHEASA-N 0.000 claims description 2
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-2-aminohexanoic acid zwitterion Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims description 2
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid zwitterion Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims description 2
- JUQLUIFNNFIIKC-YFKPBYRVSA-N L-2-aminopimelic acid Chemical compound OC(=O)[C@@H](N)CCCCC(O)=O JUQLUIFNNFIIKC-YFKPBYRVSA-N 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- AGPKZVBTJJNPAG-UHNVWZDZSA-N L-allo-isoleucine Chemical compound CC[C@@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-UHNVWZDZSA-N 0.000 claims description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 2
- OLNLSTNFRUFTLM-UHFFFAOYSA-N N-ethylasparagine Chemical compound CCNC(C(O)=O)CC(N)=O OLNLSTNFRUFTLM-UHFFFAOYSA-N 0.000 claims description 2
- 108010065338 N-ethylglycine Proteins 0.000 claims description 2
- YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine zwitterion Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 claims description 2
- KSPIYJQBLVDRRI-UHFFFAOYSA-N N-methylisoleucine Chemical compound CCC(C)C(NC)C(O)=O KSPIYJQBLVDRRI-UHFFFAOYSA-N 0.000 claims description 2
- AKCRVYNORCOYQT-UHFFFAOYSA-N N-methylvaline Chemical compound CNC(C(C)C)C(O)=O AKCRVYNORCOYQT-UHFFFAOYSA-N 0.000 claims description 2
- 229960003104 Ornithine Drugs 0.000 claims description 2
- 229940043230 Sarcosine Drugs 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 229960003692 aminobutyric acid Drugs 0.000 claims description 2
- 229960002684 aminocaproic acid Drugs 0.000 claims description 2
- 229940000635 beta-Alanine Drugs 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 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 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- PMMYEEVYMWASQN-DMTCNVIQSA-N trans-L-hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 2
- OYIFNHCXNCRBQI-UHFFFAOYSA-N α-Aminoadipic acid Chemical group OC(=O)C(N)CCCC(O)=O OYIFNHCXNCRBQI-UHFFFAOYSA-N 0.000 claims description 2
- QWCKQJZIFLGMSD-UHFFFAOYSA-N α-Aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 claims description 2
- 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 16
- 125000003118 aryl group Chemical group 0.000 claims 7
- FJHBVJOVLFPMQE-QFIPXVFZSA-N 7-Ethyl-10-Hydroxy-Camptothecin Chemical group 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 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- -1 nitro, amino Chemical group 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 230000001588 bifunctional Effects 0.000 claims 5
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrugs Drugs 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 208000008443 Pancreatic Carcinoma Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 201000005510 acute lymphocytic leukemia Diseases 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 2
- 201000011231 colorectal cancer Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000004405 heteroalkoxy group Chemical group 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- OUQGMQDVHAFXQU-UHFFFAOYSA-N 2-aminoheptanoic acid;2-amino-2-methylpropanoic acid Chemical compound CC(C)(N)C(O)=O.CCCCCC(N)C(O)=O OUQGMQDVHAFXQU-UHFFFAOYSA-N 0.000 claims 1
- 206010017758 Gastric cancer Diseases 0.000 claims 1
- 208000005017 Glioblastoma Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010061289 Metastatic neoplasm Diseases 0.000 claims 1
- DYMRYCZRMAHYKE-UHFFFAOYSA-N N-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010025310 Other lymphomas Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 208000000587 Small Cell Lung Carcinoma Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 230000001394 metastastic Effects 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 230000002209 hydrophobic Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- RDFMDVXONNIGBC-UHFFFAOYSA-N 2-aminoheptanoic acid Chemical compound CCCCCC(N)C(O)=O RDFMDVXONNIGBC-UHFFFAOYSA-N 0.000 description 1
- 229940019746 Antifibrinolytic amino acids Drugs 0.000 description 1
- SPEWLPMVLIUTHW-QFIPXVFZSA-N CC[C@](C(C=C1N2Cc3c(CC)c(cc(cc4)O)c4nc13)=C(CO1)C2=O)(C1=O)OS Chemical compound CC[C@](C(C=C1N2Cc3c(CC)c(cc(cc4)O)c4nc13)=C(CO1)C2=O)(C1=O)OS SPEWLPMVLIUTHW-QFIPXVFZSA-N 0.000 description 1
- PQNASZJZHFPQLE-LURJTMIESA-N N(6)-methyl-L-lysine Chemical compound CNCCCC[C@H](N)C(O)=O PQNASZJZHFPQLE-LURJTMIESA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- FUOOLUPWFVMBKG-UHFFFAOYSA-N α-aminoisobutanoic acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US77246406P | 2006-02-09 | 2006-02-09 | |
US60/772,464 | 2006-02-09 | ||
US80439106P | 2006-06-09 | 2006-06-09 | |
US60/804,391 | 2006-06-09 | ||
US84493806P | 2006-09-15 | 2006-09-15 | |
US60/844,938 | 2006-09-15 | ||
US86451606P | 2006-11-06 | 2006-11-06 | |
US60/864,516 | 2006-11-06 | ||
PCT/US2007/003808 WO2007092646A2 (en) | 2006-02-09 | 2007-02-09 | Multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin for treatment of breast, colorectal, pancreatic, ovarian and lung cancers |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2009526076A JP2009526076A (ja) | 2009-07-16 |
JP2009526076A5 true JP2009526076A5 (US07462627-20081209-C00021.png) | 2010-03-25 |
JP5265384B2 JP5265384B2 (ja) | 2013-08-14 |
Family
ID=38345853
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008554430A Expired - Fee Related JP5265384B2 (ja) | 2006-02-09 | 2007-02-09 | 乳癌、結腸直腸癌、膵臓癌、卵巣癌及び肺癌の治療のための7−エチル−10−ヒドロキシカンプトセシンのマルチアーム・ポリマー複合体 |
Country Status (11)
Families Citing this family (16)
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 |
JP2010518120A (ja) | 2007-02-09 | 2010-05-27 | エンゾン ファーマスーティカルズ インコーポレイテッド | 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 |
TW201010732A (en) * | 2008-08-29 | 2010-03-16 | Enzon Pharmaceuticals Inc | Method of treating RAS associated cancer |
KR20110075029A (ko) * | 2008-10-21 | 2011-07-05 | 엔즌 파마슈티칼스, 인코포레이티드 | 7-에틸-10-하이드록시캄토테신의 다중-암 고분자 컨쥬게이트로 신경모세포종의 치료 |
KR20120044925A (ko) * | 2009-04-17 | 2012-05-08 | 엔즌 파마슈티칼스, 인코포레이티드 | 7-에틸-10-하이드록시캄토테신의 다중-가지 고분자 복합체를 이용한 신생혈관형성 억제 방법 |
JP6138140B2 (ja) | 2011-10-25 | 2017-05-31 | ネクター セラピューティクス | 癌患者の治療 |
WO2014085571A1 (en) | 2012-11-28 | 2014-06-05 | Nektar Therapeutics | Method for assessing and predicting efficacy of breast cancer treatment with a long-acting topoisomerase i inhibitor |
EP3004888A1 (en) | 2013-05-31 | 2016-04-13 | Nektar Therapeutics | Method for predicting and evaluating responsiveness to cancer treatment with dna-damaging chemotherapeutic agents |
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 |
AU2015206667B2 (en) | 2014-01-14 | 2020-05-14 | Nektar Therapeutics | Combination-based treatment method |
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 |
CN106831853B (zh) * | 2017-02-15 | 2019-02-22 | 浙江海正药业股份有限公司 | 7-乙基-10-o-叔丁基二苯基硅基喜树碱-20-o-甘氨酸盐酸盐的制备工艺 |
CN108727583B (zh) * | 2017-04-21 | 2022-03-22 | 高瑞耀业(北京)科技有限公司 | 多臂靶向抗癌偶联物 |
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 |
CN108164419B (zh) * | 2017-12-25 | 2021-03-16 | 武汉大学 | 单分散聚乙二醇单甲醚修饰的丙泊酚前药的制备与应用 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5880131A (en) * | 1993-10-20 | 1999-03-09 | Enzon, Inc. | High molecular weight polymer-based prodrugs |
PT934065E (pt) * | 1996-08-30 | 2006-10-31 | Univ Hawaii | Compostos farmaceuticos |
US20040009229A1 (en) * | 2000-01-05 | 2004-01-15 | Unger Evan Charles | Stabilized nanoparticle formulations of camptotheca derivatives |
US6548488B2 (en) * | 2000-03-17 | 2003-04-15 | Aventis Pharma S.A. | Composition comprising camptothecin or a camptothecin derivative and an alkylating agent for the treatment of cancer |
US7132423B2 (en) * | 2001-09-21 | 2006-11-07 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
WO2004063200A1 (en) * | 2003-01-16 | 2004-07-29 | Techno Mart Co., Ltd | Porphyrin derivatives |
DE10307787A1 (de) * | 2003-02-24 | 2004-09-02 | Ktb Tumorforschungsgesellschaft Mbh | Protein-bindende Camptothecin-Derivate |
JP2006523237A (ja) * | 2003-04-03 | 2006-10-12 | セマフォア ファーマシューティカルズ, インコーポレイテッド | Pi−3キナーゼインヒビタープロドラッグ |
UA84420C2 (ru) * | 2003-04-11 | 2008-10-27 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | СОЕДИНЕНИЯ 1,2,4-ОКСАДИАЗОЛБЕНЗОЙНОЙ КИСЛОТЫ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ (ВАРИАНТЫ) И ПРИМЕНЕНИЕ СОЕДИНЕНИЙ ДЛЯ ЛЕЧЕНИЯ ЗАБОЛЕВАНИЯ, СВЯЗАННОГО С ПРЕЖДЕВРЕМЕННОЙ ТЕРМИНАЦИЕЙ ТРАНСЛЯЦИИ ИЛИ НОНСЕНС-ОБУСЛОВЛЕННЫМ УМЕНЬШЕНИЕМ мРНК |
TWI334868B (en) * | 2003-06-03 | 2010-12-21 | Nippon Kayaku Kk | [1,2,4] triazoro [1,5-a] pyrimidine-2-ylurea derivative and use thereof |
US20040247624A1 (en) * | 2003-06-05 | 2004-12-09 | Unger Evan Charles | Methods of making pharmaceutical formulations for the delivery of drugs having low aqueous solubility |
KR20120073370A (ko) * | 2003-09-17 | 2012-07-04 | 넥타르 테라퓨틱스 | 다분지형 고분자 전구약물 |
WO2005068424A1 (en) * | 2004-01-20 | 2005-07-28 | Cell Therapeutics Europe S.R.L. | Indolinone derivatives as receptor tyrosine kinase ihibitors |
TW200530236A (en) * | 2004-02-23 | 2005-09-16 | Chugai Pharmaceutical Co Ltd | Heteroaryl phenylurea |
ITRM20040239A1 (it) * | 2004-05-13 | 2004-08-13 | Sigma Tau Ind Farmaceuti | Derivati ciclopeptidici ad attivita' antintegrine. |
-
2007
- 2007-02-09 TW TW096104772A patent/TWI426905B/zh not_active IP Right Cessation
- 2007-02-09 CA CA002640013A patent/CA2640013A1/en not_active Abandoned
- 2007-02-09 MX MX2008010303A patent/MX2008010303A/es unknown
- 2007-02-09 ES ES07763709T patent/ES2436109T3/es active Active
- 2007-02-09 KR KR1020087021163A patent/KR20080091829A/ko not_active Application Discontinuation
- 2007-02-09 WO PCT/US2007/003808 patent/WO2007092646A2/en active Application Filing
- 2007-02-09 JP JP2008554430A patent/JP5265384B2/ja not_active Expired - Fee Related
- 2007-02-09 AU AU2007212201A patent/AU2007212201B2/en not_active Ceased
- 2007-02-09 CN CN2007800127903A patent/CN101420963B/zh not_active Expired - Fee Related
- 2007-02-09 EP EP07763709.8A patent/EP1996208B1/en not_active Not-in-force
-
2008
- 2008-07-31 IL IL193164A patent/IL193164A0/en unknown
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