JP2009544634A5 - - Google Patents
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- Publication number
- JP2009544634A5 JP2009544634A5 JP2009521137A JP2009521137A JP2009544634A5 JP 2009544634 A5 JP2009544634 A5 JP 2009544634A5 JP 2009521137 A JP2009521137 A JP 2009521137A JP 2009521137 A JP2009521137 A JP 2009521137A JP 2009544634 A5 JP2009544634 A5 JP 2009544634A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- aminoalkyl
- alkoxy
- alkyl
- thio
- 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
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 5
- -1 aryloxyimino Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 208000032839 leukemia Diseases 0.000 claims description 4
- 229940127093 camptothecin Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 210000004072 lung Anatomy 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- 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 description 2
- 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 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 210000003238 esophagus Anatomy 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 210000003128 head Anatomy 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 210000003739 neck Anatomy 0.000 claims description 2
- 150000002825 nitriles Chemical group 0.000 claims description 2
- 210000001672 ovary Anatomy 0.000 claims description 2
- 210000000496 pancreas Anatomy 0.000 claims description 2
- 210000002307 prostate Anatomy 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000005353 silylalkyl group Chemical group 0.000 claims description 2
- 229960000303 topotecan Drugs 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000002243 precursor Substances 0.000 claims 2
- MISJXUDJCSZFAH-UHFFFAOYSA-N 1-sulfanylpyridin-2-one Chemical group SN1C=CC=CC1=O MISJXUDJCSZFAH-UHFFFAOYSA-N 0.000 claims 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 238000001212 derivatisation Methods 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000012039 electrophile Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- 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
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 description 2
- PAEZRCINULFAGO-OAQYLSRUSA-N (R)-homocamptothecin Chemical compound CC[C@@]1(O)CC(=O)OCC(C2=O)=C1C=C1N2CC2=CC3=CC=CC=C3N=C21 PAEZRCINULFAGO-OAQYLSRUSA-N 0.000 description 1
- DZNNFZGDBUXWMV-ZUWDIFAMSA-N 581079-18-7 Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(OC(=O)[C@H](C)NC(=O)COCCOCC(=O)N[C@@H](C)C(=O)O[C@@]3(CC)C5=C(C(N6CC7=CC8=CC=CC=C8N=C7C6=C5)=O)COC3=O)CC)C4=NC2=C1 DZNNFZGDBUXWMV-ZUWDIFAMSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 206010065553 Bone marrow failure Diseases 0.000 description 1
- 241000759905 Camptotheca acuminata Species 0.000 description 1
- 206010011793 Cystitis haemorrhagic Diseases 0.000 description 1
- 206010059024 Gastrointestinal toxicity Diseases 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 241000209018 Nyssaceae Species 0.000 description 1
- SLOJCSGNHWIKIG-JNYZSSQASA-N afeletecan Chemical compound C([C@@H](C(=O)N[C@H](C(=O)O[C@@]1(CC)C2=C(C(N3CC4=CC5=CC=CC=C5N=C4C3=C2)=O)COC1=O)C(C)C)NC(=S)NC=1C=CC(O[C@@H]2[C@H]([C@H](OC)[C@H](O)[C@H](C)O2)O)=CC=1)C1=CNC=N1 SLOJCSGNHWIKIG-JNYZSSQASA-N 0.000 description 1
- 229950011393 afeletecan Drugs 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- LNHWXBUNXOXMRL-VWLOTQADSA-N belotecan Chemical compound C1=CC=C2C(CCNC(C)C)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 LNHWXBUNXOXMRL-VWLOTQADSA-N 0.000 description 1
- 229950011276 belotecan Drugs 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- POADTFBBIXOWFJ-VWLOTQADSA-N cositecan Chemical compound C1=CC=C2C(CC[Si](C)(C)C)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 POADTFBBIXOWFJ-VWLOTQADSA-N 0.000 description 1
- LFQCJSBXBZRMTN-OAQYLSRUSA-N diflomotecan Chemical compound CC[C@@]1(O)CC(=O)OCC(C2=O)=C1C=C1N2CC2=CC3=CC(F)=C(F)C=C3N=C21 LFQCJSBXBZRMTN-OAQYLSRUSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZVYVPGLRVWUPMP-FYSMJZIKSA-N exatecan Chemical compound C1C[C@H](N)C2=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC3=CC(F)=C(C)C1=C32 ZVYVPGLRVWUPMP-FYSMJZIKSA-N 0.000 description 1
- 229950009429 exatecan Drugs 0.000 description 1
- 231100000414 gastrointestinal toxicity Toxicity 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
- 229950009073 gimatecan Drugs 0.000 description 1
- 201000002802 hemorrhagic cystitis Diseases 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 229950009797 pegamotecan Drugs 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- VHXNKPBCCMUMSW-FQEVSTJZSA-N rubitecan Chemical compound C1=CC([N+]([O-])=O)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VHXNKPBCCMUMSW-FQEVSTJZSA-N 0.000 description 1
- 229950009213 rubitecan Drugs 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT001473A ITMI20061473A1 (it) | 2006-07-26 | 2006-07-26 | Derivati della camptotecina ad attivita antitumorale |
| ITMI2006A001473 | 2006-07-26 | ||
| PCT/EP2007/006243 WO2008011994A1 (en) | 2006-07-26 | 2007-07-13 | Camptothecin derivatives with antitumor activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009544634A JP2009544634A (ja) | 2009-12-17 |
| JP2009544634A5 true JP2009544634A5 (enExample) | 2010-08-26 |
| JP5313894B2 JP5313894B2 (ja) | 2013-10-09 |
Family
ID=38668829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009521137A Expired - Fee Related JP5313894B2 (ja) | 2006-07-26 | 2007-07-13 | 抗腫瘍活性を持つカンプトテシン誘導体 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8217053B2 (enExample) |
| EP (1) | EP2044079B1 (enExample) |
| JP (1) | JP5313894B2 (enExample) |
| KR (1) | KR101412157B1 (enExample) |
| CN (1) | CN101495486B (enExample) |
| AU (1) | AU2007278500B2 (enExample) |
| BR (1) | BRPI0714553B8 (enExample) |
| CA (1) | CA2658900C (enExample) |
| DK (1) | DK2044079T3 (enExample) |
| ES (1) | ES2561356T3 (enExample) |
| HU (1) | HUE027890T2 (enExample) |
| IL (1) | IL196653A (enExample) |
| IT (1) | ITMI20061473A1 (enExample) |
| MX (1) | MX2009000827A (enExample) |
| NO (1) | NO341812B1 (enExample) |
| PL (1) | PL2044079T3 (enExample) |
| PT (1) | PT2044079E (enExample) |
| RU (1) | RU2450008C2 (enExample) |
| SI (1) | SI2044079T1 (enExample) |
| WO (1) | WO2008011994A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10195288B2 (en) * | 2012-10-11 | 2019-02-05 | Daiichi Sankyo Company, Limited | Antibody-drug conjugate |
| EP2910573B1 (en) | 2012-10-19 | 2020-02-19 | Daiichi Sankyo Company, Limited | Antibody-drug conjugate produced by binding through linker having hydrophilic structure |
| KR101586030B1 (ko) * | 2014-01-22 | 2016-01-15 | 주식회사 엘지생활건강 | 캄프토테신을 유효성분으로 포함하는 체모 성장 억제용 조성물 |
| SG11201603960XA (en) | 2014-01-31 | 2016-07-28 | Daiichi Sankyo Co Ltd | Anti-her2 antibody-drug conjugate |
| CA2990572C (en) | 2015-06-29 | 2022-07-26 | Daiichi Sankyo Company, Limited | Method for selectively manufacturing antibody-drug conjugate |
| JPWO2018110515A1 (ja) | 2016-12-12 | 2019-10-24 | 第一三共株式会社 | 抗体−薬物コンジュゲートと免疫チェックポイント阻害剤の組み合わせ |
| SG11201906554RA (en) | 2017-01-17 | 2019-08-27 | Daiichi Sankyo Co Ltd | Anti-gpr20 antibody and anti-gpr20 antibody-drug conjugate |
| TWI926682B (zh) | 2017-05-15 | 2026-05-21 | 日商第一三共股份有限公司 | 抗體－藥物結合物之製造方法 |
| SG11202001514XA (en) | 2017-08-31 | 2020-03-30 | Daiichi Sankyo Co Ltd | Novel method for producing antibody-drug conjugate |
| EP3677589B1 (en) | 2017-08-31 | 2025-11-26 | Daiichi Sankyo Company, Limited | Improved method for producing antibody-drug conjugate |
| EP3794042B1 (en) | 2018-05-18 | 2024-03-27 | Daiichi Sankyo Co., Ltd. | Anti-muc1- exatecan antibody-drug conjugate |
| EP3831853A4 (en) | 2018-07-27 | 2022-06-01 | Daiichi Sankyo Company, Limited | ANTIBODY-DRUG CONJUGATE PROTEIN-RECOGNIZING DRUG UNIT |
| IL325918A (en) | 2018-07-31 | 2026-03-01 | Daiichi Sankyo Co Ltd | Antibody-drug conjugates for use in the treatment of metastatic brain tumor |
| US10568873B1 (en) * | 2019-02-14 | 2020-02-25 | United Arab Emirates University | Safranal-sorafenib combination therapy for liver cancer |
| CN112225745B (zh) * | 2020-11-16 | 2021-10-12 | 烟台大学 | 一种具有抗肿瘤活性的异片螺素类化合物、制备方法及用途 |
| CN114805377A (zh) * | 2021-01-29 | 2022-07-29 | 明慧医药（杭州）有限公司 | 适用于抗体-药物偶联物的毒素分子 |
| WO2022262789A1 (zh) * | 2021-06-17 | 2022-12-22 | 明慧医药（杭州）有限公司 | 一种抗肿瘤化合物及其应用 |
| CN117510515A (zh) * | 2022-07-28 | 2024-02-06 | 明慧医药（杭州）有限公司 | 适用于抗体-药物偶联物的毒素分子 |
| WO2024230752A1 (zh) * | 2023-05-08 | 2024-11-14 | 甘李药业股份有限公司 | 喜树碱衍生物、接头、配体-药物偶联物及其医药用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4391909A (en) * | 1979-03-28 | 1983-07-05 | Damon Corporation | Microcapsules containing viable tissue cells |
| US5972955A (en) | 1995-06-06 | 1999-10-26 | Dr. Reddy's Research Foundation | Water soluble C-ring analogues of 20(S)-camptothecin |
| FR2757515B1 (fr) * | 1996-12-20 | 2000-05-05 | Sod Conseils Rech Applic | Formes prodrogues et nouveaux analogues de la camptothecine, leurs procedes de preparation, leur application comme medicaments et les compositions pharmaceutiques les contenant |
| US6881555B2 (en) * | 1999-03-19 | 2005-04-19 | Aventis Pharmaceuticals Inc. | AKT nucleic acids, polypeptides, and uses thereof |
| DE60209517D1 (de) * | 2001-09-25 | 2006-04-27 | Reddys Lab Ltd Dr | Pharmazeutisch geeignete salze von 20(s)-camptothecinen |
| US20060084167A1 (en) * | 2004-10-16 | 2006-04-20 | Cohenford Menashi A | Formation of Hybrid Cells by Fusion of Lineage Committed Cells with Stem Cells |
-
2006
- 2006-07-26 IT IT001473A patent/ITMI20061473A1/it unknown
-
2007
- 2007-07-13 PT PT77860633T patent/PT2044079E/pt unknown
- 2007-07-13 US US12/374,963 patent/US8217053B2/en not_active Expired - Fee Related
- 2007-07-13 JP JP2009521137A patent/JP5313894B2/ja not_active Expired - Fee Related
- 2007-07-13 DK DK07786063.3T patent/DK2044079T3/en active
- 2007-07-13 HU HUE07786063A patent/HUE027890T2/en unknown
- 2007-07-13 AU AU2007278500A patent/AU2007278500B2/en not_active Ceased
- 2007-07-13 RU RU2009102243/04A patent/RU2450008C2/ru active
- 2007-07-13 CN CN2007800283564A patent/CN101495486B/zh not_active Expired - Fee Related
- 2007-07-13 WO PCT/EP2007/006243 patent/WO2008011994A1/en not_active Ceased
- 2007-07-13 EP EP07786063.3A patent/EP2044079B1/en active Active
- 2007-07-13 PL PL07786063T patent/PL2044079T3/pl unknown
- 2007-07-13 BR BRPI0714553A patent/BRPI0714553B8/pt not_active IP Right Cessation
- 2007-07-13 CA CA2658900A patent/CA2658900C/en not_active Expired - Fee Related
- 2007-07-13 MX MX2009000827A patent/MX2009000827A/es active IP Right Grant
- 2007-07-13 KR KR1020097001595A patent/KR101412157B1/ko not_active Expired - Fee Related
- 2007-07-13 ES ES07786063.3T patent/ES2561356T3/es active Active
- 2007-07-13 SI SI200731737T patent/SI2044079T1/sl unknown
-
2009
- 2009-01-16 NO NO20090251A patent/NO341812B1/no not_active IP Right Cessation
- 2009-01-22 IL IL196653A patent/IL196653A/en active IP Right Grant
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