CN111714498A - Quinoline derivatives for the treatment of ovarian cancer - Google Patents
Quinoline derivatives for the treatment of ovarian cancer Download PDFInfo
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- CN111714498A CN111714498A CN201910212696.7A CN201910212696A CN111714498A CN 111714498 A CN111714498 A CN 111714498A CN 201910212696 A CN201910212696 A CN 201910212696A CN 111714498 A CN111714498 A CN 111714498A
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- carboplatin
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- 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
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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Abstract
The application belongs to the field of medicines, provides a quinoline derivative for treating ovarian cancer, and particularly relates to application of 1- [ [ [4- (4-fluoro-2-methyl-1H-indol-5-yl) oxy-6-methoxyquinoline-7-yl ] oxy ] methyl ] cyclopropylamine in treatment of epithelial ovarian cancer through single-use or combined-use chemotherapeutic drugs.
Description
Technical Field
The invention belongs to the field of medicines, and particularly relates to application of a quinoline derivative in treating ovarian cancer.
Background
Tyrosine kinases are a group of enzymes catalyzing phosphorylation of tyrosine residues of proteins, play important roles in signal transduction in cells, participate in regulation, signal transmission and development of normal cells, and are closely related to proliferation, differentiation, migration and apoptosis of tumor cells. Many receptor tyrosine kinases are involved in tumor formation and are classified into Epidermal Growth Factor Receptor (EGFR), platelet-derived growth factor receptor (PDGFR), Vascular Endothelial Growth Factor Receptor (VEGFR), Fibroblast Growth Factor Receptor (FGFR), and the like according to their extracellular domain structure.
In China, the annual incidence of ovarian cancer is at the 3 rd position of female reproductive system tumors, and is located behind cervical cancer and uterine body malignant tumors, the ovarian cancer tends to rise year by year, and the mortality is located at the top of female reproductive tract malignant tumors, so the ovarian cancer is a malignant tumor seriously threatening the health of women. Ovarian malignancies encompass a variety of pathological types, the most common of which is epithelial cancer, accounting for about 70% of ovarian malignancies, followed by malignant germ cell tumors and sex cord stromal tumors, accounting for about 20% and 5% of each. The main pathological types of ovarian epithelial cancer are: serous carcinoma (80%), endometrioid carcinoma (10%), clear cell carcinoma (10%), mucinous carcinoma (3%), among others, there are some other rare pathological types. Among them, serous carcinomas are the most common and classified into low-grade (LGSC) and high-grade serous carcinomas (HGSC). At the gene level, low-grade serous carcinomas have high frequencies of KRAS and BRAF mutations, but rarely TP53 mutations; high grade serous carcinomas are characterized by a genetically high instability and a mutation in TP53 in almost all cases.
Disclosure of Invention
The invention provides an application of a compound I or a pharmaceutically acceptable salt, a hydrate or a prodrug thereof in preparing a medicament for treating ovarian epithelial cancer. Preferred are pharmaceutically acceptable salts of compound I. The epithelial carcinoma of the ovary is preferably clear cell carcinoma.
The present invention provides a method of treating epithelial carcinoma of the ovary comprising: administering to a patient in need thereof an effective amount of compound I or a pharmaceutically acceptable salt, hydrate or prodrug thereof. Preferred are pharmaceutically acceptable salts of compound I. The epithelial carcinoma of the ovary is preferably clear cell carcinoma.
In another aspect, the present invention provides a pharmaceutical composition comprising: (i) compound I or a pharmaceutically acceptable salt, hydrate or prodrug thereof; (ii) optionally a chemotherapeutic agent.
In a further aspect, the present invention provides the use of a pharmaceutical composition for the manufacture of a medicament for the treatment of epithelial ovarian cancer, said pharmaceutical composition comprising: (i) compound I or a pharmaceutically acceptable salt, hydrate or prodrug thereof; (ii) optionally a chemotherapeutic agent. The epithelial carcinoma of the ovary is preferably clear cell carcinoma.
In yet another aspect, the invention provides a method of treating epithelial carcinoma of the ovary, comprising: administering to a patient in need thereof an effective amount of (I) compound I or a pharmaceutically acceptable salt, hydrate or prodrug thereof; (ii) optionally a chemotherapeutic agent.
In some embodiments, the present invention provides a method of treating clear cell carcinoma comprising: administering to a patient in need thereof an effective amount of (I) compound I or a pharmaceutically acceptable salt, hydrate or prodrug thereof; (ii) optionally a chemotherapeutic agent.
In the present invention, compound I has the chemical name of 1- [ [ [4- (4-fluoro-2-methyl-1H-indol-5-yl) oxy-6-methoxyquinolin-7-yl ] oxy ] methyl ] cyclopropylamine, which has the following structural formula:
in the present invention, the prodrug of compound I is converted in vivo to the free base form of compound I. Pharmaceutically acceptable salts of compound I, which salts can be generated from various organic and inorganic acids according to methods well known in the art. "pharmaceutically acceptable salts" include, but are not limited to, acid addition salts formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like; or with organic acids such as acetic, trifluoroacetic, propionic, hexanoic, heptanoic, cyclopentanepropionic, glycolic, pyruvic, lactic, malonic, succinic, malic, maleic, fumaric, tartaric, citric, benzoic, cinnamic, mandelic, methanesulfonic, ethanesulfonic, 1, 2-ethanedisulfonic, 2-hydroxyethanesulfonic, benzenesulfonic, p-chlorobenzenesulfonic, p-toluenesulfonic, 3-phenylpropionic, trimethylacetic, t-butylacetic, dodecylsulfuric, gluconic, glutamic, hydroxynaphthoic, salicylic, aliphatic acids and the like. In some embodiments, the pharmaceutically acceptable salt of compound I is the hydrochloride salt of compound I. In some embodiments, the pharmaceutically acceptable salt of compound I is the monohydrochloride salt of compound I. In some embodiments, the pharmaceutically acceptable salt of compound I is the dihydrochloride salt of compound I. In some embodiments, the hydrochloride salt of compound I is in a crystalline form. In some embodiments, the pharmaceutically acceptable salt of compound I is a crystalline form of compound I dihydrochloride. In some embodiments, the pharmaceutically acceptable salt of compound I is the maleate salt of compound I.
In the present invention, the optional chemotherapeutic agent is selected from: one or two or three of paclitaxel, carboplatin, bevacizumab, doxorubicin liposome, docetaxel, bleomycin, etoposide, cisplatin, gemcitabine, albumin-bound paclitaxel, 5-FU, leucovorin, oxaliplatin, topotecan, hexamethylmelamine, capecitabine, ifosfamide, irinotecan, pemetrexed and vinorelbine. The chemotherapeutic drugs are preferably: paclitaxel in combination with carboplatin, doxorubicin liposome in combination with carboplatin, docetaxel in combination with carboplatin, carboplatin and paclitaxel in combination with bevacizumab, gemcitabine in combination with carboplatin, gemcitabine and bevacizumab in combination with carboplatin, gemcitabine in combination with cisplatin, albumin bound paclitaxel in combination with carboplatin. In the present invention, the ovarian cancer is epithelial cancer. In particular, the main pathological types of epithelial ovarian cancer are: serous carcinoma, endometrioid carcinoma, clear cell carcinoma, mucinous carcinoma, and in some embodiments, the ovarian cancer is clear cell carcinoma. In some embodiments, the ovarian cancer is a treatment-progressing ovarian cancer. The ovarian cancer progressed through treatment refers to ovarian cancer progressed after being treated by a first-line treatment scheme or a second-line treatment scheme, or a third-line treatment scheme.
Each component of the pharmaceutical composition of the present invention may optionally be used in combination with one or more pharmaceutically acceptable carriers, wherein each component may independently, or some or all of them together contain a pharmaceutically acceptable carrier and/or excipient. The pharmaceutical compositions of the present invention may be formulated separately from each other, or some or all of them may be co-formulated. Preferably, the components of the pharmaceutical composition are formulated separately or each formulated into a suitable pharmaceutical composition. In some embodiments, the pharmaceutical compositions of the present application may be formulated as pharmaceutical compositions suitable for single or multiple administrations. In some particular embodiments, the pharmaceutical composition containing compound I or a pharmaceutically acceptable salt, hydrate or prodrug thereof may be selected from solid pharmaceutical compositions including, but not limited to, tablets or capsules.
The components of the pharmaceutical composition of the present invention may be administered each separately, or some or all of them may be co-administered. The components of the pharmaceutical compositions of the present invention may be administered substantially simultaneously, or some or all of them may be administered substantially simultaneously. The components of the pharmaceutical composition of the present invention may be administered independently of each other, or some or all of them together in a suitable route, including, but not limited to, oral or parenteral (by intravenous, intramuscular, topical or subcutaneous routes). In some embodiments, the components of the pharmaceutical composition of the invention may each be administered independently, or some or all of them together orally or by injection, for example intravenously or intraperitoneally.
The components of the pharmaceutical composition of the present invention may be each independently, or some or all of them together in a suitable dosage form, including, but not limited to, tablets, troches, pills, capsules (e.g., hard capsules, soft capsules, enteric capsules, microcapsules), elixirs, granules, syrups, injections (intramuscular, intravenous, intraperitoneal), granules, emulsions, suspensions, solutions, dispersions, and sustained release formulations for oral or non-oral administration.
In the present invention, the components of the pharmaceutical composition may be administered to a patient as separate entities (e.g., pharmaceutical compositions) simultaneously, alternately or sequentially, wherein the active ingredient is administered to the patient to a therapeutically effective amount level. The individual active ingredients may be packaged, sold or administered as completely separate pharmaceutical compositions.
The amount of each component in the pharmaceutical composition of the present invention administered may be determined by the severity of the disease, the response to the disease, any treatment-related toxicities, the age and health of the patient. In some embodiments, the daily dose of compound I, or a pharmaceutically acceptable salt, hydrate, or prodrug thereof, administered is from 6 mg to 20 mg; preferably 8 mg to 16 mg; more preferably 8 mg to 14 mg; most preferably 8 mg, 10mg or 12 mg. Compound I or a pharmaceutically acceptable salt, hydrate or prodrug thereof may be administered once or more times daily, preferably once daily; in some embodiments, compound I or a pharmaceutically acceptable salt, hydrate or prodrug thereof is administered once daily in an oral solid formulation.
The dosage regimen may be determined in combination with the activity, toxicity of the drug, and patient tolerance. In general, the components of the pharmaceutical compositions of the present invention may be administered according to dosing regimens well known in the art. In some embodiments, compound I, or a pharmaceutically acceptable salt, hydrate, or prodrug thereof, is administered in a staggered dosing pattern; the interval administration comprises an administration period and a drug stopping period, and can be administered once or more times per day in the administration period. In some embodiments, the ratio of the dosing period to the rest period in days is 2:0.5 to 5, preferably 2:0.5 to 3, more preferably 2:0.5 to 2, more preferably 2:0.5 to 1. In some embodiments, the administration is discontinued for 1 week for 2 weeks. In certain particular embodiments, compound I, or a pharmaceutically acceptable salt, hydrate, or prodrug thereof, is administered orally at a dose of 8, 10, and/or 12mg once daily for 2 weeks, and 1 week off.
Herein, unless otherwise indicated, the dosages and ranges provided herein are based on the molecular weight of the free base of the active ingredient. As used herein and for purposes of the present invention, the following terms used in the specification and claims shall have the following meanings, unless otherwise indicated.
By "patient" is meant a mammal, preferably a human.
By "pharmaceutically acceptable" is meant that it is used in the preparation of a medicament that is generally safe, non-toxic, and neither biologically nor otherwise undesirable, and includes that it is acceptable for human pharmaceutical use.
By "therapeutically effective amount" is meant an amount of a compound that, when administered to a human for the treatment of a disease, is sufficient to effect treatment for the disease.
By "treatment" is meant any administration of a therapeutically effective amount of a compound and includes:
(1) inhibiting the disease (i.e., arresting the further development of the pathology and/or symptomatology) in a human experiencing or exhibiting the pathology or symptomatology of the disease, or
(2) Ameliorating the disease (i.e., reversing the pathology and/or symptomatology) in a human experiencing or exhibiting the pathology or symptomatology of the disease.
"treatment failure" refers to intolerance of toxic side effects, disease progression during treatment, or relapse after treatment is complete.
"optionally" means with or without.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are only for illustrating the present invention and are not intended to limit the scope of the present invention.
Example 1
Patients 1, 53 years old, ECOG-PS score 1, no smoking history, no family history of malignant tumor, 2 years ago in local hospitals, "Whole uterus + right adnexal tumor + left adnexal resection", postoperative pathology prompts of FIGO staged IA phase (assisted by 6-cycle PC scheme) 2018 for 3 months, PET-CT image examination results of 1, uterus resection + bilateral adnexal resection, multiple nodular and strip FDG metabolic increase focus of peritoneum, considering peritoneal extensive implantation metastasis, right ventricular lymph node with FDG metabolic increase, considering metastasis possibly large, abdominopelvic fluid 2, sphenoid inflammation, other examinations, CA125: 426U/ml, later, other hospital pathology examination results are re-diagnosed, diagnosis (right ovarian) clear cell carcinoma is shown, bone marrow C: PAX-8+, HNF β +, WT 32 +, WT1-, Ki-67+ 30%, first-cycle 2-line platinum + 547 alcohol, chemotherapy is given to patients, peritoneal dialysis is given to patients, and peritoneal dialysis is given to patients, peritoneal dialysis is given to patients, peritoneal dialysis isMinimum 2 x 10 platelets9L, failure to continue to tolerate chemotherapy. The three-line treatment is carried out by Nilaparib (Niraparib)300mg po qd, side effects can be tolerated, chest distress and short breath symptoms appear after 1 month of taking, malignant pleural effusion appears after 1 month of applying the Nilaparib for treatment, and the progress is evaluated. CA125: 328U/ml.
The anrotinib hydrochloride capsules (10 mg standard, 1 time daily, 2 weeks for continuous medication and 1 week off, i.e. one administration cycle every 3 weeks) were administered starting at 8/1/2018.
After 3 months, the images are seen:
"post-ovarian cancer": for example, the uterus is deficient, the local soft tissue shadow of the bladder posterior wall area is slightly strengthened after strengthening, the local punctate compact shadow is seen, the peritoneum is irregularly thickened, the peritoneum, the omentum majus and the mesenterium area are frequently seen with nodule shadows, the strengthening is seen, and the peritoneum cake is marked. Large amount of hydrops in abdominal cavity and pelvic cavity.
Liver: the shape and size are basically normal, speckled calcific foci are seen in the liver, and no obvious abnormal intensified foci are seen after the liver is strengthened. The blood vessels in the liver normally run, the main trunk of the portal vein is not widened, and the cavity is not full of defects. The intrahepatic and extrahepatic bile ducts are not obviously expanded.
Gallbladder: no obvious abnormality in shape and size, and no positive calculus shadow in the cavity.
Pancreas: the pancreas is still uniform in substantial density, the boundary is clear, and the main pancreatic duct is not obviously expanded.
Spleen: spleen is frequently infected with calcified lesion.
Kidney: the shape and size of the two kidneys are basically normal, and the left kidney is like a bursa, so that the enhancement is not enhanced.
Adrenal gland: no obvious space occupying focus is seen in bilateral adrenal gland area.
Bladder: the bladder has a poor filling and the wall is slightly thickened.
And (3) diagnosis results:
(1) after ovarian cancer operation, wide planting and transferring in abdominal cavity and peritoneum are considered, and the number of the cells is slightly reduced compared with 2018-09-05CT tablets; large amount of hydrops in abdominal cavity and pelvic cavity.
(2) Liver and spleen are multiple calcified foci.
(3) Left renal cyst.
(4) Thickening of the bladder wall, please combine clinically.
Changes in CA125 after chemotherapy in patients are shown in table 1.
TABLE 1
Claims (7)
1. The application of the compound I or the pharmaceutically acceptable salt, the hydrate or the prodrug thereof in preparing the medicines for treating the epithelial ovarian cancer,
2. use of a pharmaceutical composition for the manufacture of a medicament for the treatment of epithelial ovarian cancer, said pharmaceutical composition comprising: (i) compound I or a pharmaceutically acceptable salt, hydrate or prodrug thereof; (ii) optionally a chemotherapeutic agent, wherein the chemotherapeutic agent is selected from the group consisting of: one or two or three of paclitaxel, carboplatin, bevacizumab, doxorubicin liposome, docetaxel, bleomycin, etoposide, cisplatin, gemcitabine, albumin-bound paclitaxel, 5-FU, leucovorin, oxaliplatin, topotecan, hexamethylmelamine, capecitabine, ifosfamide, irinotecan, pemetrexed and vinorelbine.
3. Use according to claim 2, characterized in that the chemotherapeutic agent is selected from the group consisting of paclitaxel in combination with carboplatin, doxorubicin liposome in combination with carboplatin, docetaxel in combination with carboplatin, carboplatin in combination with paclitaxel, bevacizumab gemcitabine in combination with carboplatin, gemcitabine and bevacizumab in combination with carboplatin, gemcitabine in combination with cisplatin, albumin-bound paclitaxel in combination with carboplatin.
4. Use according to claims 1 to 3, characterized in that the epithelial cancer of the ovary is a clear cell carcinoma.
5. A method of treating epithelial carcinoma of the ovary, comprising: administering to a patient in need thereof an effective amount of (I) compound I or a pharmaceutically acceptable salt, hydrate or prodrug thereof; (ii) optionally a chemotherapeutic agent.
6. The method of claim 5, wherein the epithelial carcinoma of the ovary is clear cell carcinoma.
7. The method of claims 5 and 6, wherein the chemotherapeutic agents include, but are not limited to: one or two or three of paclitaxel, carboplatin, bevacizumab, doxorubicin liposome, docetaxel, bleomycin, etoposide, cisplatin, gemcitabine, albumin-bound paclitaxel, 5-FU, leucovorin, oxaliplatin, topotecan, hexamethylmelamine, capecitabine, ifosfamide, irinotecan, pemetrexed and vinorelbine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910212696.7A CN111714498A (en) | 2019-03-20 | 2019-03-20 | Quinoline derivatives for the treatment of ovarian cancer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910212696.7A CN111714498A (en) | 2019-03-20 | 2019-03-20 | Quinoline derivatives for the treatment of ovarian cancer |
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| Publication Number | Publication Date |
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| CN111714498A true CN111714498A (en) | 2020-09-29 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201910212696.7A Withdrawn CN111714498A (en) | 2019-03-20 | 2019-03-20 | Quinoline derivatives for the treatment of ovarian cancer |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483319A (en) * | 2007-03-14 | 2014-01-01 | 南京爱德程医药科技有限公司 | Spiro substituted compounds as angiogenesis inhibitors |
| CN105213394A (en) * | 2014-06-06 | 2016-01-06 | 正大天晴药业集团股份有限公司 | There is the quinoline of anti-tumor activity |
-
2019
- 2019-03-20 CN CN201910212696.7A patent/CN111714498A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483319A (en) * | 2007-03-14 | 2014-01-01 | 南京爱德程医药科技有限公司 | Spiro substituted compounds as angiogenesis inhibitors |
| CN105213394A (en) * | 2014-06-06 | 2016-01-06 | 正大天晴药业集团股份有限公司 | There is the quinoline of anti-tumor activity |
Non-Patent Citations (2)
| Title |
|---|
| 无: "NCT02558348", 《CLINICALTRIALS.GOV》 * |
| 无: "安罗替尼联合培美曲塞 卵巢上皮癌", 《中国临床试验注册中心》 * |
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