CN112402425A - 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
- CN112402425A CN112402425A CN202011350126.3A CN202011350126A CN112402425A CN 112402425 A CN112402425 A CN 112402425A CN 202011350126 A CN202011350126 A CN 202011350126A CN 112402425 A CN112402425 A CN 112402425A
- Authority
- CN
- China
- Prior art keywords
- dinitrophenyl
- pyrazolo
- drug
- tumor
- oxazine
- 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
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 36
- 206010059866 Drug resistance Diseases 0.000 title claims abstract description 24
- 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 claims abstract description 12
- 239000012313 reversal agent Substances 0.000 title claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 45
- 229940079593 drug Drugs 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 102000013013 Member 2 Subfamily G ATP Binding Cassette Transporter Human genes 0.000 claims description 15
- 108010090306 Member 2 Subfamily G ATP Binding Cassette Transporter Proteins 0.000 claims description 15
- 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 claims description 10
- 229960001156 mitoxantrone Drugs 0.000 claims description 9
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 6
- 102000004169 proteins and genes Human genes 0.000 claims description 6
- 108090000623 proteins and genes Proteins 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- XIBUCANHNLRVFI-UHFFFAOYSA-N 6-(3,5-dinitrophenyl)-1-phenylpyrazolo[3,4-d][1,3]oxazin-4-one Chemical group [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 claims description 4
- 229940045799 anthracyclines and related substance Drugs 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 229940126062 Compound A Drugs 0.000 claims description 3
- 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 3
- 229940034982 antineoplastic agent Drugs 0.000 claims description 3
- 229960004679 doxorubicin Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 229940009456 adriamycin Drugs 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 230000036436 anti-hiv Effects 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 239000003435 antirheumatic agent Substances 0.000 claims description 2
- 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 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 239000003018 immunosuppressive agent Substances 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000002417 nutraceutical Substances 0.000 claims description 2
- 235000021436 nutraceutical agent Nutrition 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 239000006186 oral dosage form Substances 0.000 claims description 2
- 239000006201 parenteral dosage form Substances 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000008174 sterile solution Substances 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 238000013268 sustained release Methods 0.000 claims description 2
- 239000012730 sustained-release form Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 239000006208 topical dosage form Substances 0.000 claims description 2
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims description 2
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims description 2
- 241000700605 Viruses Species 0.000 claims 1
- 208000035269 cancer or benign tumor Diseases 0.000 claims 1
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
- 210000004881 tumor cell Anatomy 0.000 abstract description 12
- -1 3, 5-dinitrophenyl Chemical group 0.000 abstract description 10
- 238000011160 research Methods 0.000 abstract description 9
- 238000011282 treatment Methods 0.000 abstract description 9
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 7
- 230000002441 reversible effect Effects 0.000 abstract description 7
- 230000035945 sensitivity Effects 0.000 abstract description 7
- 238000009098 adjuvant therapy Methods 0.000 abstract description 2
- 238000002512 chemotherapy Methods 0.000 abstract description 2
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- 238000011260 co-administration Methods 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 11
- 230000036457 multidrug resistance Effects 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 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
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 3
- 230000002018 overexpression Effects 0.000 description 3
- 239000013641 positive control Substances 0.000 description 3
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 3
- 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
- 238000002835 absorbance Methods 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 229940044683 chemotherapy drug Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000011287 therapeutic dose Methods 0.000 description 2
- 206010009944 Colon cancer Diseases 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
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 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
- 208000029742 colonic neoplasm Diseases 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
- 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
- 230000006872 improvement 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
- 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
- 230000000699 topical effect Effects 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
- 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 (10)
- The application of 3, 5-dinitrophenyl-pyrazolo [3,4-d ] [1,3] oxazine as tumor drug resistance reversal agent is provided.
- 3. the use of claim 1, wherein the tumor resistance-reversing agent is a transport pump inhibitor;preferably, the tumor drug resistance reversal agent is a drug-resistant protein transport inhibitor;more preferably, the tumor-resistant drug is mitoxantrone or doxorubicin.
- Application of 3, 5-dinitrophenyl-pyrazolo [3,4-d ] [1,3] oxazine in preparation of drugs with inhibition effect on drug-resistant protein (ABCG 2).
- 6. a pharmaceutical composition, comprising: compound a and a pharmaceutically acceptable carrier;wherein the compound A is 3, 5-dinitrophenyl-pyrazolo [3,4-d ] [1,3] oxazine.
- 7. The pharmaceutical composition according to claim 6, wherein compound A is 1-phenyl-6- (3, 5-dinitrophenyl) -pyrazolo [3,4-d ] [1,3] oxazin-4 (1H) -one.
- 8. The pharmaceutical composition of claim 6, further comprising a drug for treating or adjunctively treating a tumor;preferably, the drugs for treating or assisting in treating tumors include, but are not limited to, camptothecin analogs, tyrosine kinase inhibitors, anthracyclines, anti-HIV virus drugs, antirheumatic drugs, immunosuppressants and antibiotics;or the medicine for treating the tumor is an ABCG2 medicine-resistance related medicine; or the anthracycline medicine is mitoxantrone or adriamycin;or, the pharmaceutical composition includes, but is not limited to, oral dosage forms, parenteral dosage forms, topical dosage forms, and rectal dosage forms; preferably, the pharmaceutical composition may be tablets, capsules, pills, powders, sustained release formulations, solutions and suspensions for oral administration, sterile solutions, suspensions or emulsions for parenteral injection, ointments or creams for external use, or suppositories for rectal administration.
- 9. Use of a pharmaceutical composition according to any one of claims 6 to 8 for the preparation of an anti-tumor agent.
- 10. The use of a compound or pharmaceutical composition of claim 9 in the preparation of an anti-neoplastic agent, wherein the anti-neoplastic agent comprises a drug for treating a neoplasm, a nutraceutical, and a model tool drug.
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 |
---|---|
CN112402425A true CN112402425A (en) | 2021-02-26 |
CN112402425B CN112402425B (en) | 2021-12-03 |
Family
ID=74843242
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
Country Status (1)
Country | Link |
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CN (1) | CN112402425B (en) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111388477A (en) * | 2020-04-24 | 2020-07-10 | 山东师范大学 | Application of 2-phenylpyrazole [1,5-a ] pyrimidine compound as tumor drug resistance reversal agent |
CN111467341A (en) * | 2020-04-24 | 2020-07-31 | 山东师范大学 | Application of 3, 4-dimethoxyphenyl-benzo [ d ] oxazole as tumor drug resistance reversal agent |
-
2020
- 2020-11-26 CN CN202011350126.3A patent/CN112402425B/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111388477A (en) * | 2020-04-24 | 2020-07-10 | 山东师范大学 | Application of 2-phenylpyrazole [1,5-a ] pyrimidine compound as tumor drug resistance reversal agent |
CN111467341A (en) * | 2020-04-24 | 2020-07-31 | 山东师范大学 | Application of 3, 4-dimethoxyphenyl-benzo [ d ] oxazole as tumor drug resistance reversal agent |
Non-Patent Citations (3)
Title |
---|
CHE,JUN等: "Traceless solid-phase Synthesis of Heteroannulated 1,3-Oxazin-6-ones", 《JOURNAL OF COMBINATORIAL CHEMISTRY》 * |
刘蒙等: "多种结肠癌5-氟尿嘧啶耐药细胞株的建立及耐药机制初步研究", 《中国普通外科杂志》 * |
江明华等主编: "《生化药理学》", 31 August 2004 * |
Also Published As
Publication number | Publication date |
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CN112402425B (en) | 2021-12-03 |
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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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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 |