ES2628022T3 - Derivados de camptotecina con actividad antitumoral - Google Patents
Derivados de camptotecina con actividad antitumoral Download PDFInfo
- Publication number
- ES2628022T3 ES2628022T3 ES07786096.3T ES07786096T ES2628022T3 ES 2628022 T3 ES2628022 T3 ES 2628022T3 ES 07786096 T ES07786096 T ES 07786096T ES 2628022 T3 ES2628022 T3 ES 2628022T3
- Authority
- ES
- Spain
- Prior art keywords
- hydrogen
- aminoalkyl
- alkoxy
- hydroxy
- groups
- 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.)
- Active
Links
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 title description 5
- 230000000259 anti-tumor effect Effects 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- -1 aryloxyamino Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 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 abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 150000002825 nitriles Chemical group 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 125000005353 silylalkyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 10
- 125000000033 alkoxyamino group Chemical group 0.000 claims abstract 2
- 229940127093 camptothecin Drugs 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 238000001212 derivatisation Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 4
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229960000303 topotecan Drugs 0.000 description 3
- 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 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 108020004414 DNA Proteins 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000002688 persistence Effects 0.000 description 2
- 102100021888 Helix-loop-helix protein 1 Human genes 0.000 description 1
- 101000897691 Homo sapiens Helix-loop-helix protein 1 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000002784 cytotoxicity assay Methods 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 208000023958 prostate neoplasm Diseases 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI20061474 | 2006-07-26 | ||
| IT001474A ITMI20061474A1 (it) | 2006-07-26 | 2006-07-26 | Derivati della camptotecina ad attivita antitumorale |
| PCT/EP2007/006294 WO2008012003A1 (en) | 2006-07-26 | 2007-07-16 | Camptothecin derivatives with antitumor activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2628022T3 true ES2628022T3 (es) | 2017-08-01 |
Family
ID=38668855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07786096.3T Active ES2628022T3 (es) | 2006-07-26 | 2007-07-16 | Derivados de camptotecina con actividad antitumoral |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8193210B2 (enExample) |
| EP (1) | EP2044080B1 (enExample) |
| JP (1) | JP5313895B2 (enExample) |
| KR (1) | KR101496374B1 (enExample) |
| CN (1) | CN101495485B (enExample) |
| AU (1) | AU2007278509B2 (enExample) |
| BR (1) | BRPI0714672B8 (enExample) |
| CA (1) | CA2658902C (enExample) |
| DK (1) | DK2044080T3 (enExample) |
| ES (1) | ES2628022T3 (enExample) |
| IL (1) | IL196652A0 (enExample) |
| IT (1) | ITMI20061474A1 (enExample) |
| MX (1) | MX2009000828A (enExample) |
| NO (1) | NO342506B1 (enExample) |
| PL (1) | PL2044080T3 (enExample) |
| PT (1) | PT2044080T (enExample) |
| RU (1) | RU2450007C2 (enExample) |
| SI (1) | SI2044080T1 (enExample) |
| WO (1) | WO2008012003A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9379559B2 (en) | 2012-02-03 | 2016-06-28 | International Business Machines Corporation | System and method of charging a vehicle using a dynamic power grid, and system and method of managing power consumption in the vehicle |
| PL235836B1 (pl) | 2012-10-25 | 2020-11-02 | Inst Chemii Organicznej Polskiej Akademii Nauk | Pochodne kamptotecyny, sposób ich otrzymywania i zastosowanie |
| CN108690036B (zh) * | 2018-05-22 | 2021-05-25 | 北京海步医药科技股份有限公司 | 一种10-二氟甲基喜树碱类化合物及其制备方法和应用 |
| LU102067B1 (en) | 2020-09-17 | 2022-03-18 | Narodowy Inst Lekow | 7-Ethyl-10-hydroxycamptothecin derivatives for use in the treatment of cancer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5972955A (en) * | 1995-06-06 | 1999-10-26 | Dr. Reddy's Research Foundation | Water soluble C-ring analogues of 20(S)-camptothecin |
| IT1282673B1 (it) * | 1996-02-23 | 1998-03-31 | Ist Naz Stud Cura Dei Tumori | Derivati della camptotecina e loro uso come agenti antitumorali |
-
2006
- 2006-07-26 IT IT001474A patent/ITMI20061474A1/it unknown
-
2007
- 2007-07-16 EP EP07786096.3A patent/EP2044080B1/en active Active
- 2007-07-16 PT PT77860963T patent/PT2044080T/pt unknown
- 2007-07-16 WO PCT/EP2007/006294 patent/WO2008012003A1/en not_active Ceased
- 2007-07-16 MX MX2009000828A patent/MX2009000828A/es active IP Right Grant
- 2007-07-16 PL PL07786096T patent/PL2044080T3/pl unknown
- 2007-07-16 RU RU2009102241/04A patent/RU2450007C2/ru active
- 2007-07-16 ES ES07786096.3T patent/ES2628022T3/es active Active
- 2007-07-16 JP JP2009521140A patent/JP5313895B2/ja not_active Expired - Fee Related
- 2007-07-16 SI SI200731933A patent/SI2044080T1/sl unknown
- 2007-07-16 KR KR1020097001596A patent/KR101496374B1/ko not_active Expired - Fee Related
- 2007-07-16 CN CN2007800281978A patent/CN101495485B/zh not_active Expired - Fee Related
- 2007-07-16 DK DK07786096.3T patent/DK2044080T3/en active
- 2007-07-16 BR BRPI0714672A patent/BRPI0714672B8/pt not_active IP Right Cessation
- 2007-07-16 AU AU2007278509A patent/AU2007278509B2/en not_active Ceased
- 2007-07-16 CA CA2658902A patent/CA2658902C/en not_active Expired - Fee Related
- 2007-07-16 US US12/373,834 patent/US8193210B2/en not_active Expired - Fee Related
-
2009
- 2009-01-16 NO NO20090252A patent/NO342506B1/no not_active IP Right Cessation
- 2009-01-22 IL IL196652A patent/IL196652A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN101495485B (zh) | 2012-04-11 |
| BRPI0714672B1 (pt) | 2020-10-20 |
| BRPI0714672B8 (pt) | 2021-05-25 |
| CA2658902C (en) | 2014-09-23 |
| CA2658902A1 (en) | 2008-01-31 |
| NO20090252L (no) | 2009-01-16 |
| CN101495485A (zh) | 2009-07-29 |
| KR20090032100A (ko) | 2009-03-31 |
| WO2008012003A1 (en) | 2008-01-31 |
| US8193210B2 (en) | 2012-06-05 |
| NO342506B1 (no) | 2018-06-04 |
| RU2450007C2 (ru) | 2012-05-10 |
| IL196652A0 (en) | 2009-11-18 |
| MX2009000828A (es) | 2009-02-03 |
| BRPI0714672A2 (pt) | 2013-03-26 |
| AU2007278509A1 (en) | 2008-01-31 |
| PL2044080T3 (pl) | 2017-10-31 |
| PT2044080T (pt) | 2017-06-15 |
| US20100010032A1 (en) | 2010-01-14 |
| EP2044080A1 (en) | 2009-04-08 |
| HK1135692A1 (en) | 2010-06-11 |
| JP2010500971A (ja) | 2010-01-14 |
| SI2044080T1 (sl) | 2017-07-31 |
| EP2044080B1 (en) | 2017-05-10 |
| AU2007278509B2 (en) | 2012-10-04 |
| JP5313895B2 (ja) | 2013-10-09 |
| RU2009102241A (ru) | 2010-07-27 |
| ITMI20061474A1 (it) | 2008-01-27 |
| DK2044080T3 (en) | 2017-07-17 |
| KR101496374B1 (ko) | 2015-03-04 |
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