EA039764B1 - Соль n-(2,6-диэтилфенил)-8-({4-[4-(диметиламино)пиперидин-1-ил]-2-метоксифенил}амино)-1-метил-4,5-дигидро-1h-пиразоло[4,3-h]хиназолин-3-карбоксамида, ее получение и препараты, которые ее содержат - Google Patents
Соль n-(2,6-диэтилфенил)-8-({4-[4-(диметиламино)пиперидин-1-ил]-2-метоксифенил}амино)-1-метил-4,5-дигидро-1h-пиразоло[4,3-h]хиназолин-3-карбоксамида, ее получение и препараты, которые ее содержат Download PDFInfo
- Publication number
- EA039764B1 EA039764B1 EA202090115A EA202090115A EA039764B1 EA 039764 B1 EA039764 B1 EA 039764B1 EA 202090115 A EA202090115 A EA 202090115A EA 202090115 A EA202090115 A EA 202090115A EA 039764 B1 EA039764 B1 EA 039764B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- quinazoline
- pyrazolo
- amino
- dimethylamino
- piperidin
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title description 12
- 239000000203 mixture Substances 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 6
- BDWQUAIODJREAF-UHFFFAOYSA-N n-(2,6-diethylphenyl)-8-[4-[4-(dimethylamino)piperidin-1-yl]-2-methoxyanilino]-1-methyl-4,5-dihydropyrazolo[4,3-h]quinazoline-3-carboxamide Chemical compound CCC1=CC=CC(CC)=C1NC(=O)C1=NN(C)C(C2=N3)=C1CCC2=CN=C3NC1=CC=C(N2CCC(CC2)N(C)C)C=C1OC BDWQUAIODJREAF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 36
- 206010028980 Neoplasm Diseases 0.000 claims description 31
- UCAVIZKQSBARGL-UHFFFAOYSA-N 2h-quinazoline-3-carboxamide Chemical compound C1=CC=CC2=CN(C(=O)N)CN=C21 UCAVIZKQSBARGL-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 229910019142 PO4 Inorganic materials 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 16
- 239000010452 phosphate Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 230000003394 haemopoietic effect Effects 0.000 claims description 10
- 210000001519 tissue Anatomy 0.000 claims description 10
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 6
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 6
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 6
- 201000009030 Carcinoma Diseases 0.000 claims description 5
- 210000004072 lung Anatomy 0.000 claims description 5
- 206010027406 Mesothelioma Diseases 0.000 claims description 4
- 210000003169 central nervous system Anatomy 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 210000001428 peripheral nervous system Anatomy 0.000 claims description 4
- 210000003491 skin Anatomy 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 3
- 206010003571 Astrocytoma Diseases 0.000 claims description 3
- 208000003950 B-cell lymphoma Diseases 0.000 claims description 3
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 3
- 201000008808 Fibrosarcoma Diseases 0.000 claims description 3
- 208000032612 Glial tumor Diseases 0.000 claims description 3
- 206010018338 Glioma Diseases 0.000 claims description 3
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 3
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 3
- 206010029260 Neuroblastoma Diseases 0.000 claims description 3
- 206010042971 T-cell lymphoma Diseases 0.000 claims description 3
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 3
- 210000000481 breast Anatomy 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 210000001072 colon Anatomy 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 210000003734 kidney Anatomy 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 201000008968 osteosarcoma Diseases 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims description 3
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 3
- 210000001685 thyroid gland Anatomy 0.000 claims description 3
- 102000001253 Protein Kinase Human genes 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 108060006633 protein kinase Proteins 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 102100040678 Programmed cell death protein 1 Human genes 0.000 claims 2
- 101710089372 Programmed cell death protein 1 Proteins 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 claims 1
- 239000005551 L01XE03 - Erlotinib Substances 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 208000033781 Thyroid carcinoma Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 229960002756 azacitidine Drugs 0.000 claims 1
- 229960004562 carboplatin Drugs 0.000 claims 1
- 190000008236 carboplatin Chemical group 0.000 claims 1
- 208000019065 cervical carcinoma Diseases 0.000 claims 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 claims 1
- 229960001433 erlotinib Drugs 0.000 claims 1
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims 1
- 231100000024 genotoxic Toxicity 0.000 claims 1
- 230000001738 genotoxic effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- BMGQWWVMWDBQGC-IIFHNQTCSA-N midostaurin Chemical compound CN([C@H]1[C@H]([C@]2(C)O[C@@H](N3C4=CC=CC=C4C4=C5C(=O)NCC5=C5C6=CC=CC=C6N2C5=C43)C1)OC)C(=O)C1=CC=CC=C1 BMGQWWVMWDBQGC-IIFHNQTCSA-N 0.000 claims 1
- 229950010895 midostaurin Drugs 0.000 claims 1
- 230000000394 mitotic effect Effects 0.000 claims 1
- JLYAXFNOILIKPP-KXQOOQHDSA-N navitoclax Chemical compound C([C@@H](NC1=CC=C(C=C1S(=O)(=O)C(F)(F)F)S(=O)(=O)NC(=O)C1=CC=C(C=C1)N1CCN(CC1)CC1=C(CCC(C1)(C)C)C=1C=CC(Cl)=CC=1)CSC=1C=CC=CC=1)CN1CCOCC1 JLYAXFNOILIKPP-KXQOOQHDSA-N 0.000 claims 1
- 229950004847 navitoclax Drugs 0.000 claims 1
- 230000002611 ovarian Effects 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- QOFFJEBXNKRSPX-ZDUSSCGKSA-N pemetrexed Chemical compound C1=N[C]2NC(N)=NC(=O)C2=C1CCC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 QOFFJEBXNKRSPX-ZDUSSCGKSA-N 0.000 claims 1
- 229960005079 pemetrexed Drugs 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 239000002574 poison Substances 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 201000001514 prostate carcinoma Diseases 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 201000008261 skin carcinoma Diseases 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- 150000004579 taxol derivatives Chemical class 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 208000013077 thyroid gland carcinoma Diseases 0.000 claims 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims 1
- 229960004528 vincristine Drugs 0.000 claims 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims 1
- BRQRTBHRMBBOCZ-UHFFFAOYSA-N OP(O)(O)=O.CCc1cccc(CC)c1NC(=O)c1nn(C)c-2c1CCc1cnc(Nc3ccc(cc3OC)N3CCC(CC3)N(C)C)nc-21 Chemical compound OP(O)(O)=O.CCc1cccc(CC)c1NC(=O)c1nn(C)c-2c1CCc1cnc(Nc3ccc(cc3OC)N3CCC(CC3)N(C)C)nc-21 BRQRTBHRMBBOCZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012458 free base Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 239000000843 powder Substances 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 11
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- -1 4-bromo-2-methoxyphenyl Chemical group 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 208000035269 cancer or benign tumor Diseases 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 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 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 2
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 208000023275 Autoimmune disease Diseases 0.000 description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
- 208000011691 Burkitt lymphomas Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 2
- 229910002483 Cu Ka Inorganic materials 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 201000006107 Familial adenomatous polyposis Diseases 0.000 description 2
- 206010016935 Follicular thyroid cancer Diseases 0.000 description 2
- 206010018364 Glomerulonephritis Diseases 0.000 description 2
- 208000017604 Hodgkin disease Diseases 0.000 description 2
- 208000021519 Hodgkin lymphoma Diseases 0.000 description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 2
- 101000962483 Homo sapiens Max dimerization protein 1 Proteins 0.000 description 2
- 101001000302 Homo sapiens Max-interacting protein 1 Proteins 0.000 description 2
- 101000896484 Homo sapiens Mitotic checkpoint protein BUB3 Proteins 0.000 description 2
- 101000896657 Homo sapiens Mitotic checkpoint serine/threonine-protein kinase BUB1 Proteins 0.000 description 2
- 101000794228 Homo sapiens Mitotic checkpoint serine/threonine-protein kinase BUB1 beta Proteins 0.000 description 2
- 101000957106 Homo sapiens Mitotic spindle assembly checkpoint protein MAD1 Proteins 0.000 description 2
- 101000957259 Homo sapiens Mitotic spindle assembly checkpoint protein MAD2A Proteins 0.000 description 2
- 208000007766 Kaposi sarcoma Diseases 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 102100039185 Max dimerization protein 1 Human genes 0.000 description 2
- 102100035880 Max-interacting protein 1 Human genes 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 102100021718 Mitotic checkpoint protein BUB3 Human genes 0.000 description 2
- 102100021691 Mitotic checkpoint serine/threonine-protein kinase BUB1 Human genes 0.000 description 2
- 102100030144 Mitotic checkpoint serine/threonine-protein kinase BUB1 beta Human genes 0.000 description 2
- 101000590284 Mus musculus 26S proteasome non-ATPase regulatory subunit 14 Proteins 0.000 description 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 208000009905 Neurofibromatoses Diseases 0.000 description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 2
- 208000031481 Pathologic Constriction Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 201000010208 Seminoma Diseases 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 206010048218 Xeroderma Diseases 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 208000036878 aneuploidy Diseases 0.000 description 2
- 231100001075 aneuploidy Toxicity 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 230000001363 autoimmune Effects 0.000 description 2
- 210000003679 cervix uteri Anatomy 0.000 description 2
- 208000029664 classic familial adenomatous polyposis Diseases 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- MXFYYFVVIIWKFE-UHFFFAOYSA-N dicyclohexyl-[2-[2,6-di(propan-2-yloxy)phenyl]phenyl]phosphane Chemical compound CC(C)OC1=CC=CC(OC(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 MXFYYFVVIIWKFE-UHFFFAOYSA-N 0.000 description 2
- 210000003238 esophagus Anatomy 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 210000000232 gallbladder Anatomy 0.000 description 2
- 206010021198 ichthyosis Diseases 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 230000017205 mitotic cell cycle checkpoint Effects 0.000 description 2
- YFJAIURZMRJPDB-UHFFFAOYSA-N n,n-dimethylpiperidin-4-amine Chemical compound CN(C)C1CCNCC1 YFJAIURZMRJPDB-UHFFFAOYSA-N 0.000 description 2
- 208000007538 neurilemmoma Diseases 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 201000004931 neurofibromatosis Diseases 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 210000001672 ovary Anatomy 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 230000002980 postoperative effect Effects 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 208000005069 pulmonary fibrosis Diseases 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 208000037803 restenosis Diseases 0.000 description 2
- 206010039667 schwannoma Diseases 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 208000037804 stenosis Diseases 0.000 description 2
- 230000036262 stenosis Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 208000001608 teratocarcinoma Diseases 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 2
- 210000003932 urinary bladder Anatomy 0.000 description 2
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- 235000012431 wafers Nutrition 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 239000008364 bulk solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012907 medicinal substance Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/42—Phosphorus; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Inorganic Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17305826 | 2017-06-29 | ||
| PCT/EP2018/067394 WO2019002454A1 (en) | 2017-06-29 | 2018-06-28 | NOVEL N- (2,6-DIETHYLPHENYL) -8 - ({4- [4- (DIMETHYLAMINO) PIPERIDIN-1-YL] -2-METHOXYPHENYL} AMINO) -1-METHYL-4,5-DIHYDRO-1H SALT -PYRAZOLO [4,3-H] QUINAZOLINE-3-CARBOXAMIDE, ITS PREPARATION AND FORMULATIONS CONTAINING THE SAME |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA202090115A1 EA202090115A1 (ru) | 2020-05-25 |
| EA039764B1 true EA039764B1 (ru) | 2022-03-11 |
Family
ID=59313166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA202090115A EA039764B1 (ru) | 2017-06-29 | 2018-06-28 | Соль n-(2,6-диэтилфенил)-8-({4-[4-(диметиламино)пиперидин-1-ил]-2-метоксифенил}амино)-1-метил-4,5-дигидро-1h-пиразоло[4,3-h]хиназолин-3-карбоксамида, ее получение и препараты, которые ее содержат |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US11160806B2 (enExample) |
| EP (1) | EP3645535B1 (enExample) |
| JP (1) | JP7141416B2 (enExample) |
| KR (1) | KR102609333B1 (enExample) |
| CN (1) | CN110896636B (enExample) |
| AR (1) | AR112040A1 (enExample) |
| AU (1) | AU2018293729B9 (enExample) |
| CA (1) | CA3068357C (enExample) |
| CL (1) | CL2019003848A1 (enExample) |
| EA (1) | EA039764B1 (enExample) |
| ES (1) | ES2900048T3 (enExample) |
| IL (1) | IL271628B2 (enExample) |
| MA (1) | MA49498A (enExample) |
| PL (1) | PL3645535T3 (enExample) |
| SG (1) | SG11201912651WA (enExample) |
| TW (1) | TWI750393B (enExample) |
| UY (1) | UY37778A (enExample) |
| WO (1) | WO2019002454A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025002962A1 (en) | 2023-06-30 | 2025-01-02 | Nerviano Medical Sciences S.R.L. | Use of a mps1 inhibitor for the treatment of hepatocellular carcinoma |
| WO2025021587A1 (en) | 2023-07-21 | 2025-01-30 | Nerviano Medical Sciences S.R.L. | Combination of a mps1 inhibitor and immune checkpoint inhibitors, uses and pharmaceutical compositions thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2303891A1 (en) * | 2008-06-26 | 2011-04-06 | Nerviano Medical Sciences S.r.l. | Pyrazolo-quinazolines |
-
2018
- 2018-06-21 UY UY0001037778A patent/UY37778A/es not_active Application Discontinuation
- 2018-06-28 EP EP18732820.8A patent/EP3645535B1/en active Active
- 2018-06-28 CA CA3068357A patent/CA3068357C/en active Active
- 2018-06-28 TW TW107122235A patent/TWI750393B/zh active
- 2018-06-28 KR KR1020207002339A patent/KR102609333B1/ko active Active
- 2018-06-28 ES ES18732820T patent/ES2900048T3/es active Active
- 2018-06-28 JP JP2019572116A patent/JP7141416B2/ja active Active
- 2018-06-28 AU AU2018293729A patent/AU2018293729B9/en active Active
- 2018-06-28 AR ARP180101781A patent/AR112040A1/es unknown
- 2018-06-28 MA MA049498A patent/MA49498A/fr unknown
- 2018-06-28 US US16/624,488 patent/US11160806B2/en active Active
- 2018-06-28 EA EA202090115A patent/EA039764B1/ru unknown
- 2018-06-28 CN CN201880043442.0A patent/CN110896636B/zh active Active
- 2018-06-28 WO PCT/EP2018/067394 patent/WO2019002454A1/en not_active Ceased
- 2018-06-28 PL PL18732820T patent/PL3645535T3/pl unknown
- 2018-06-28 SG SG11201912651WA patent/SG11201912651WA/en unknown
-
2019
- 2019-12-22 IL IL271628A patent/IL271628B2/en unknown
- 2019-12-26 CL CL2019003848A patent/CL2019003848A1/es unknown
-
2021
- 2021-09-30 US US17/490,318 patent/US20220016122A1/en not_active Abandoned
-
2024
- 2024-07-01 US US18/760,494 patent/US20240350501A1/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2303891A1 (en) * | 2008-06-26 | 2011-04-06 | Nerviano Medical Sciences S.r.l. | Pyrazolo-quinazolines |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201904971A (zh) | 2019-02-01 |
| CL2019003848A1 (es) | 2020-07-10 |
| CA3068357C (en) | 2022-04-19 |
| US11160806B2 (en) | 2021-11-02 |
| UY37778A (es) | 2019-01-31 |
| AU2018293729A1 (en) | 2020-01-23 |
| CA3068357A1 (en) | 2019-01-03 |
| US20220016122A1 (en) | 2022-01-20 |
| US20240350501A1 (en) | 2024-10-24 |
| AR112040A1 (es) | 2019-09-11 |
| PL3645535T3 (pl) | 2022-03-21 |
| BR112019027924A2 (pt) | 2020-08-18 |
| TWI750393B (zh) | 2021-12-21 |
| IL271628A (en) | 2020-02-27 |
| IL271628B2 (en) | 2023-07-01 |
| EP3645535A1 (en) | 2020-05-06 |
| KR102609333B1 (ko) | 2023-12-01 |
| JP2020525477A (ja) | 2020-08-27 |
| MA49498A (fr) | 2021-05-26 |
| EP3645535B1 (en) | 2021-09-08 |
| IL271628B1 (en) | 2023-03-01 |
| CN110896636B (zh) | 2022-07-19 |
| AU2018293729B2 (en) | 2022-03-10 |
| AU2018293729B9 (en) | 2022-07-14 |
| US20200246339A1 (en) | 2020-08-06 |
| SG11201912651WA (en) | 2020-01-30 |
| JP7141416B2 (ja) | 2022-09-22 |
| KR20200020905A (ko) | 2020-02-26 |
| WO2019002454A1 (en) | 2019-01-03 |
| EA202090115A1 (ru) | 2020-05-25 |
| CN110896636A (zh) | 2020-03-20 |
| ES2900048T3 (es) | 2022-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5851990B2 (ja) | Ｐｌｋ阻害剤の塩 | |
| CN111148745A (zh) | Fgfr抑制剂的结晶形式及其制备方法 | |
| KR20190120458A (ko) | 결정질의 (8s,9r)-5-플루오로-8-(4-플루오로페닐)-9-(1-메틸-1h-1,2,4-트리아졸-5-일)-8,9-디하이드로-2h-피리도[4,3,2-de]프탈라진-3(7h)-온 토실레이트 염 | |
| KR20170032330A (ko) | Ｃ-Ｍｅｔ 억제제의 결정질 유리 염기 또는 이의 결정질 산 염, 및 이들의 제조방법 및 용도 | |
| US20240350501A1 (en) | SALT OF N-(2,6-DIETHYLPHENYL)-8-({4-[4-(DIMETHYLAMINO) PIPERIDIN-1-YL]-2-METHOXYPHENYL}AMINO)-1-METHYL-4,5-DIHYDRO-1H-PYRAZOLO[4,3-h]QUINAZOLINE-3-CARBOXAMIDE, ITS PREPARATION, AND FORMULATIONS CONTAINING IT | |
| AU2019218186B2 (en) | Urea-substituted aromatic ring-linked dioxinoquinoline compounds, preparation method and uses thereof | |
| CN120379987A (zh) | 嘧啶化合物的新型晶型和包含其的药物组合物以及其使用方法 | |
| EP3077392B1 (en) | Crystalline forms of n-(4-((3-(2-amino-4-pyrimidinyl) - 2-pyridinyl)oxy)phenyl)-4-(4-methyl - 2-thienyl)-1-phthalazinamine pharmaceutically acceptable salts and uses thereof | |
| TW202023562A (zh) | 喹唑啉化合物及其鹽酸鹽之結晶形態 | |
| KR20210024004A (ko) | Cdk4/6의 활성을 억제하기 위한 화합물의 결정 형태 및 그것의 용도 | |
| WO2024235289A1 (zh) | 用于egfr蛋白降解的化合物及其用途 | |
| WO2023093859A1 (zh) | Axl激酶抑制剂的盐、其制备方法和用途 | |
| EP3750894B1 (en) | Urea-substituted aromatic ring-linked dioxazoline compound, preparation method therefor, and uses thereof | |
| HK40022862A (en) | Salt of a compound inhibiting mps1 kinase, its preparation and formulations containing it | |
| HK40022862B (en) | Salt of a compound inhibiting mps1 kinase, its preparation and formulations containing it | |
| BR112019027924B1 (pt) | Fosfato de n-(2,6-dietilfenil)-8-({4-[4-(dimetilamino)piperidin-1-il]-2- metoxifenil}amino)-1-metil-4,5-di-hidro-1h-pirazolo[4,3-h]quinazolina-3- carboxamida, processo para a sua obtenção, composição farmacêutica, combinação e seus usos | |
| HK40003818A (en) | Polymorphs of gdc-0032, methods of production, and pharmaceutical uses thereof | |
| HK1223101A1 (zh) | Gdc-0032的多晶型物、其制备方法和药物用途 |