NZ771365B2 - Tetrahydropyranyl amino-pyrrolopyrimidinone and methods of use thereof - Google Patents
Tetrahydropyranyl amino-pyrrolopyrimidinone and methods of use thereof Download PDFInfo
- Publication number
- NZ771365B2 NZ771365B2 NZ771365A NZ77136515A NZ771365B2 NZ 771365 B2 NZ771365 B2 NZ 771365B2 NZ 771365 A NZ771365 A NZ 771365A NZ 77136515 A NZ77136515 A NZ 77136515A NZ 771365 B2 NZ771365 B2 NZ 771365B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- lymphoma
- cancer
- carcinoma
- leukemia
- cell
- Prior art date
Links
- QBCYEGVJTIOUCK-UHFFFAOYSA-N 4-amino-6-(oxan-2-yl)pyrrolo[3,2-d]pyrimidin-2-one Chemical compound O1C(CCCC1)C1=CC=2C(C(=NC(N=2)=O)N)=N1 QBCYEGVJTIOUCK-UHFFFAOYSA-N 0.000 title 1
- 102100029823 Tyrosine-protein kinase BTK Human genes 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000012453 solvate Substances 0.000 claims abstract 2
- 206010028980 Neoplasm Diseases 0.000 claims 10
- 201000011510 cancer Diseases 0.000 claims 10
- 206010025323 Lymphomas Diseases 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 4
- 230000035772 mutation Effects 0.000 claims 4
- 210000003169 central nervous system Anatomy 0.000 claims 3
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
- 208000003950 B-cell lymphoma Diseases 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 229940124291 BTK inhibitor Drugs 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 208000028018 Lymphocytic leukaemia Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 206010039491 Sarcoma Diseases 0.000 claims 2
- 210000003679 cervix uteri Anatomy 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 2
- 208000003747 lymphoid leukemia Diseases 0.000 claims 2
- 210000000214 mouth Anatomy 0.000 claims 2
- 208000025113 myeloid leukemia Diseases 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims 1
- 208000003200 Adenoma Diseases 0.000 claims 1
- 206010001233 Adenoma benign Diseases 0.000 claims 1
- 206010073478 Anaplastic large-cell lymphoma Diseases 0.000 claims 1
- 208000028564 B-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims 1
- 206010048832 Colon adenoma Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 206010073069 Hepatic cancer Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 206010023347 Keratoacanthoma Diseases 0.000 claims 1
- 239000002177 L01XE27 - Ibrutinib Substances 0.000 claims 1
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 1
- 208000032004 Large-Cell Anaplastic Lymphoma Diseases 0.000 claims 1
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 201000010208 Seminoma Diseases 0.000 claims 1
- 208000016025 Waldenstroem macroglobulinemia Diseases 0.000 claims 1
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 claims 1
- 208000009956 adenocarcinoma Diseases 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 238000001574 biopsy Methods 0.000 claims 1
- 201000001531 bladder carcinoma Diseases 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 210000000133 brain stem Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 210000000621 bronchi Anatomy 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 1
- 230000002357 endometrial effect Effects 0.000 claims 1
- 210000003238 esophagus Anatomy 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- XYFPWWZEPKGCCK-GOSISDBHSA-N ibrutinib Chemical group C1=2C(N)=NC=NC=2N([C@H]2CN(CCC2)C(=O)C=C)N=C1C(C=C1)=CC=C1OC1=CC=CC=C1 XYFPWWZEPKGCCK-GOSISDBHSA-N 0.000 claims 1
- 229960001507 ibrutinib Drugs 0.000 claims 1
- 210000003228 intrahepatic bile duct Anatomy 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 210000000244 kidney pelvis Anatomy 0.000 claims 1
- 208000003849 large cell carcinoma Diseases 0.000 claims 1
- 210000002429 large intestine Anatomy 0.000 claims 1
- 210000000867 larynx Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 210000000088 lip Anatomy 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 201000002250 liver carcinoma Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000005249 lung adenocarcinoma Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 201000010198 papillary carcinoma Diseases 0.000 claims 1
- 210000003800 pharynx Anatomy 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 210000000664 rectum Anatomy 0.000 claims 1
- 201000010174 renal carcinoma Diseases 0.000 claims 1
- 210000003491 skin Anatomy 0.000 claims 1
- 208000000649 small cell carcinoma Diseases 0.000 claims 1
- 210000000813 small intestine Anatomy 0.000 claims 1
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 210000002105 tongue Anatomy 0.000 claims 1
- 208000010576 undifferentiated carcinoma Diseases 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract 1
- 239000002207 metabolite Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
Abstract
The application relates to a compound of Formula (I): or a pharmaceutically acceptable salt thereof, tautomer, prodrug, solvate, metabolite, polymorph, analog or derivative thereof, which modulates the activity of BTK, a pharmaceutical composition comprising the compound of Formula (I), and a method of treating or preventing a disease in which BTK plays a role.
Claims (22)
1. Use of a compound of Formula (I): or a pharmaceutically acceptable salt, tautomer, or solvate, thereof, in the manufacture of a medicament for treating cancer in a subject in need thereof, wherein a mutant BTK is detected in a sample from the subject.
2. The use of claim 1, wherein the mutant BTK comprises a drug-resistant mutation.
3. The use of claim 2, wherein the drug-resistant mutation is a mutation at amino acid
4. The use of claim 2, wherein the drug-resistant mutation is C481S.
5. The use of any one of the preceding claims, wherein the cancer is resistant to a BTK inhibitor.
6. The use of claim 5, wherein the BTK inhibitor is ibrutinib.
7. The use of any one of the preceding claims, wherein the cancer is selected from breast, ovary, cervix, prostate, testis, genitourinary tract, esophagus, larynx, stomach, skin, lung, bone, colon, pancreas, thyroid, hairy cells, buccal cavity, naso-pharyngeal, pharynx, lip, tongue, mouth, small intestine, colon-rectum, large intestine, rectum, brain and central nervous system, bronchus, liver, intrahepatic bile duct, endometrial, kidney, renal pelvis, urinary bladder, uterine corpus, uterine cervix, or oral cavity, neuroblastoma, keratoacanthoma, epidermoid carcinoma, large cell carcinoma, non-small cell lung carcinoma (NSCLC), small cell carcinoma, lung adenocarcinoma, adenoma, adenocarcinoma, follicular carcinoma, undifferentiated carcinoma, papillary carcinoma, seminoma, melanoma, sarcoma, bladder carcinoma, liver carcinoma, kidney carcinoma, myeloid disorders, lymphoma, Hodgkin's leukemia, hepatocellular cancer, glioma/glioblastoma, multiple myeloma, acute myelogenous leukemia, chronic myelogenous leukemia, lymphocytic leukemia, chronic lymphoid leukemia (CLL), myeloid leukemia, non-Hodgkin lymphoma, and villous colon adenoma.
8. The use of any one of the preceding claims, wherein the cancer is chronic lymphoid leukemia.
9. The use of any one of claims 1-7, wherein the cancer is lymphoma.
10. The use of claim 9, wherein the lymphoma is non-Hodgkin lymphoma.
11. The use of claim 9, wherein the lymphoma is diffuse large B-cell lymphoma.
12. The use of claim 9, wherein the lymphoma is mantle cell lymphoma.
13. The use of claim 9, wherein the lymphoma is B-cell lymphoma.
14. The use of claim 13, wherein the B-cell lymphoma is B-cell non-Hodgkin lymphoma.
15. The use of claim 9, wherein the lymphoma is anaplastic large cell lymphoma, central nervous system (CNS) lymphoma, or Waldenstrom macroglobulinemia.
16. The use of any one of claims 1-7, wherein the cancer is myeloid disorders or myeloid leukemia.
17. The use of any one of claims 1-7, wherein the cancer is acute myelogenous leukemia or chronic myelogenous leukemia.
18. The use of any one of claims 1-7, wherein the cancer is multiple myeloma.
19. The use of any one of claims 1-7, wherein the cancer is lymphocytic leukemia.
20. The use of any one of claims 1-7, wherein the cancer is sarcoma or brain tumor.
21. The use of any one of the preceding claims, wherein the sample is a tissue or biopsy from the subject.
22. The use according to any one of claim 1 to 21, substantially as herein described with reference to any example thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ771365A NZ771365B2 (en) | 2015-12-23 | Tetrahydropyranyl amino-pyrrolopyrimidinone and methods of use thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ771365A NZ771365B2 (en) | 2015-12-23 | Tetrahydropyranyl amino-pyrrolopyrimidinone and methods of use thereof | |
| NZ743384A NZ743384B2 (en) | 2015-12-23 | Tetrahydropyranyl amino-pyrrolopyrimidinone and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ771365A NZ771365A (en) | 2024-05-31 |
| NZ771365B2 true NZ771365B2 (en) | 2024-09-03 |
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