CN112402425B - Application of 3, 5-dinitrophenyl-pyrazolo [3,4-d ] [1,3] oxazine as tumor drug resistance reversal agent - Google Patents
Application of 3, 5-dinitrophenyl-pyrazolo [3,4-d ] [1,3] oxazine as tumor drug resistance reversal agent Download PDFInfo
- Publication number
- CN112402425B CN112402425B CN202011350126.3A CN202011350126A CN112402425B CN 112402425 B CN112402425 B CN 112402425B CN 202011350126 A CN202011350126 A CN 202011350126A CN 112402425 B CN112402425 B CN 112402425B
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- China
- Prior art keywords
- tumor
- dinitrophenyl
- pyrazolo
- drug resistance
- oxazine
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- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 33
- 206010059866 Drug resistance Diseases 0.000 title claims abstract description 24
- 239000012313 reversal agent Substances 0.000 title claims abstract description 12
- VNBZKARPPZQORA-UHFFFAOYSA-N 3-(3,5-dinitrophenyl)pyrazolo[3,4-d][1,3]oxazine Chemical compound [N+](=O)([O-])C=1C=C(C=C(C=1)[N+](=O)[O-])C1=NN=C2N=COC=C21 VNBZKARPPZQORA-UHFFFAOYSA-N 0.000 title abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 34
- 229940079593 drug Drugs 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 16
- -1 3, 5-dinitrophenyl Chemical group 0.000 claims abstract description 13
- 238000011282 treatment Methods 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 229960001156 mitoxantrone Drugs 0.000 claims description 9
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical group O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 9
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- 229940126062 Compound A Drugs 0.000 claims description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 3
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 description 3
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 3
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 3
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- 102000005416 ATP-Binding Cassette Transporters Human genes 0.000 description 2
- 108010006533 ATP-Binding Cassette Transporters Proteins 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
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- 229940045799 anthracyclines and related substance Drugs 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- 238000011287 therapeutic dose Methods 0.000 description 2
- XIBUCANHNLRVFI-UHFFFAOYSA-N 6-(3,5-dinitrophenyl)-1-phenylpyrazolo[3,4-d][1,3]oxazin-4-one Chemical class [O-][N+](=O)C1=CC([N+](=O)[O-])=CC(C=2OC(=O)C=3C=NN(C=3N=2)C=2C=CC=CC=2)=C1 XIBUCANHNLRVFI-UHFFFAOYSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 239000005517 L01XE01 - Imatinib Substances 0.000 description 1
- 239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 229940009456 adriamycin Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 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 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 238000001516 cell proliferation assay Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 1
- 229960002584 gefitinib Drugs 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 description 1
- 229960002411 imatinib Drugs 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002417 nutraceutical Substances 0.000 description 1
- 235000021436 nutraceutical agent Nutrition 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000006208 topical dosage form Substances 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/136—Amines having aromatic rings, e.g. ketamine, nortriptyline having the amino group directly attached to the aromatic ring, e.g. benzeneamine
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011350126.3A CN112402425B (en) | 2020-11-26 | 2020-11-26 | Application of 3, 5-dinitrophenyl-pyrazolo [3,4-d ] [1,3] oxazine as tumor drug resistance reversal agent |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011350126.3A CN112402425B (en) | 2020-11-26 | 2020-11-26 | Application of 3, 5-dinitrophenyl-pyrazolo [3,4-d ] [1,3] oxazine as tumor drug resistance reversal agent |
Publications (2)
Publication Number | Publication Date |
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CN112402425A CN112402425A (en) | 2021-02-26 |
CN112402425B true CN112402425B (en) | 2021-12-03 |
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Family Applications (1)
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CN202011350126.3A Active CN112402425B (en) | 2020-11-26 | 2020-11-26 | Application of 3, 5-dinitrophenyl-pyrazolo [3,4-d ] [1,3] oxazine as tumor drug resistance reversal agent |
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CN (1) | CN112402425B (en) |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN111388477B (en) * | 2020-04-24 | 2021-06-25 | 山东师范大学 | Application of 2-phenylpyrazole [1,5-a ] pyrimidine compound as tumor drug resistance reversal agent |
CN111467341B (en) * | 2020-04-24 | 2021-05-11 | 山东师范大学 | Application of 3, 4-dimethoxyphenyl-benzo [ d ] oxazole as tumor drug resistance reversal agent |
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2020
- 2020-11-26 CN CN202011350126.3A patent/CN112402425B/en active Active
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CN112402425A (en) | 2021-02-26 |
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TR01 | Transfer of patent right |
Effective date of registration: 20230411 Address after: 2081, building a, 88 Jianghai West Road, Liangxi District, Wuxi City, Jiangsu Province, 214000 Patentee after: Wuxi Xiangyuan Information Technology Co.,Ltd. Address before: 250014 No. 88, Wenhua East Road, Lixia District, Shandong, Ji'nan Patentee before: SHANDONG NORMAL University |
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TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20240430 Address after: 201400 Building 1, No.1 Haikun Road, Fengxian District, Shanghai Patentee after: Shanghai Xianglihe Pharmaceutical Co.,Ltd. Country or region after: China Address before: 2081, building a, 88 Jianghai West Road, Liangxi District, Wuxi City, Jiangsu Province, 214000 Patentee before: Wuxi Xiangyuan Information Technology Co.,Ltd. Country or region before: China |
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TR01 | Transfer of patent right |