CA3174316A1 - Crystalline ret inhibitor - Google Patents
Crystalline ret inhibitor Download PDFInfo
- Publication number
- CA3174316A1 CA3174316A1 CA3174316A CA3174316A CA3174316A1 CA 3174316 A1 CA3174316 A1 CA 3174316A1 CA 3174316 A CA3174316 A CA 3174316A CA 3174316 A CA3174316 A CA 3174316A CA 3174316 A1 CA3174316 A1 CA 3174316A1
- Authority
- CA
- Canada
- Prior art keywords
- selpercatinib
- acid
- slurry
- cancer
- water
- 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.)
- Pending
Links
- 101150077555 Ret gene Proteins 0.000 title description 4
- 239000003112 inhibitor Substances 0.000 title description 4
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 claims abstract description 156
- 238000000034 method Methods 0.000 claims abstract description 153
- 229940121610 selpercatinib Drugs 0.000 claims abstract description 54
- 101000579425 Homo sapiens Proto-oncogene tyrosine-protein kinase receptor Ret Proteins 0.000 claims abstract description 42
- 102100028286 Proto-oncogene tyrosine-protein kinase receptor Ret Human genes 0.000 claims abstract description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 144
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 109
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 107
- 150000001875 compounds Chemical class 0.000 claims description 91
- 239000000203 mixture Substances 0.000 claims description 91
- 239000002904 solvent Substances 0.000 claims description 82
- 239000002002 slurry Substances 0.000 claims description 80
- 239000013078 crystal Substances 0.000 claims description 74
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 55
- -1 hydrazine compound Chemical class 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 238000003756 stirring Methods 0.000 claims description 34
- 206010028980 Neoplasm Diseases 0.000 claims description 32
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 31
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 30
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 30
- 239000007787 solid Substances 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 26
- 201000011510 cancer Diseases 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 238000001816 cooling Methods 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 16
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 15
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 239000003638 chemical reducing agent Substances 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 230000004927 fusion Effects 0.000 claims description 11
- 201000005202 lung cancer Diseases 0.000 claims description 11
- 208000020816 lung neoplasm Diseases 0.000 claims description 11
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 11
- 238000001228 spectrum Methods 0.000 claims description 11
- 239000012351 deprotecting agent Substances 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 10
- 238000004922 13C solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims description 9
- 208000009018 Medullary thyroid cancer Diseases 0.000 claims description 9
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 9
- 239000012346 acetyl chloride Substances 0.000 claims description 9
- 208000023356 medullary thyroid gland carcinoma Diseases 0.000 claims description 9
- CTAIEPPAOULMFY-UHFFFAOYSA-N 6-methoxypyridine-3-carbaldehyde Chemical compound COC1=CC=C(C=O)C=N1 CTAIEPPAOULMFY-UHFFFAOYSA-N 0.000 claims description 8
- QHYZFTNTVXUBOP-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-3-carbonitrile Chemical compound C1=CC=CC2=C(C#N)C=NN21 QHYZFTNTVXUBOP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 8
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 208000006876 Multiple Endocrine Neoplasia Type 2b Diseases 0.000 claims description 6
- 206010073148 Multiple endocrine neoplasia type 2A Diseases 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 6
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 6
- 125000006242 amine protecting group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
- 208000015799 differentiated thyroid carcinoma Diseases 0.000 claims description 6
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 201000002510 thyroid cancer Diseases 0.000 claims description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 238000003828 vacuum filtration Methods 0.000 claims description 6
- 238000010899 nucleation Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
- 150000000996 L-ascorbic acids Chemical class 0.000 claims description 3
- 206010033701 Papillary thyroid cancer Diseases 0.000 claims description 3
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 3
- 229960005070 ascorbic acid Drugs 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- 201000010881 cervical cancer Diseases 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 210000004877 mucosa Anatomy 0.000 claims description 3
- 201000010279 papillary renal cell carcinoma Diseases 0.000 claims description 3
- 208000025061 parathyroid hyperplasia Diseases 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 208000028591 pheochromocytoma Diseases 0.000 claims description 3
- 230000000306 recurrent effect Effects 0.000 claims description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 3
- 208000030045 thyroid gland papillary carcinoma Diseases 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 2
- 201000009030 Carcinoma Diseases 0.000 claims description 2
- 210000003123 bronchiole Anatomy 0.000 claims description 2
- 201000005249 lung adenocarcinoma Diseases 0.000 claims description 2
- 210000005265 lung cell Anatomy 0.000 claims description 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 229940125905 RET kinase inhibitor Drugs 0.000 abstract 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 208000037765 diseases and disorders Diseases 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 64
- 239000000243 solution Substances 0.000 description 36
- 239000012453 solvate Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 21
- 238000002425 crystallisation Methods 0.000 description 21
- 230000008025 crystallization Effects 0.000 description 19
- 239000000463 material Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 16
- 238000002474 experimental method Methods 0.000 description 15
- 239000000523 sample Substances 0.000 description 14
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
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- 150000001298 alcohols Chemical class 0.000 description 10
- 238000002955 isolation Methods 0.000 description 10
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- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
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- DVFXLNFDWATPMW-IWOKLKJTSA-N tert-butyldiphenylsilyl Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C(C)(C)C)[C@@H](OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](CC(O2)N2C3=NC=NC(N)=C3N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)O)C1 DVFXLNFDWATPMW-IWOKLKJTSA-N 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 238000004481 total suppression of sideband Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- IARSSOVWSJAVSZ-UHFFFAOYSA-N tris(dimethylamino)sulfanium Chemical compound CN(C)[S+](N(C)C)N(C)C IARSSOVWSJAVSZ-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07D487/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- A61K31/4995—Pyrazines or piperazines forming part of bridged 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
-
- 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
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202063011701P | 2020-04-17 | 2020-04-17 | |
| US63/011,701 | 2020-04-17 | ||
| US202163151354P | 2021-02-19 | 2021-02-19 | |
| US63/151,354 | 2021-02-19 | ||
| PCT/US2021/026611 WO2021211380A1 (en) | 2020-04-17 | 2021-04-09 | Crystalline ret inhibitor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3174316A1 true CA3174316A1 (en) | 2021-10-21 |
Family
ID=75747118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3174316A Pending CA3174316A1 (en) | 2020-04-17 | 2021-04-09 | Crystalline ret inhibitor |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP4136090A1 (ja) |
| JP (1) | JP2023522012A (ja) |
| KR (1) | KR20230002706A (ja) |
| CN (1) | CN115916791A (ja) |
| AU (1) | AU2021255488A1 (ja) |
| BR (1) | BR112022020446A2 (ja) |
| CA (1) | CA3174316A1 (ja) |
| CL (1) | CL2022002849A1 (ja) |
| CO (1) | CO2022014882A2 (ja) |
| CR (1) | CR20220520A (ja) |
| DO (1) | DOP2022000221A (ja) |
| EC (1) | ECSP22080982A (ja) |
| IL (1) | IL297212A (ja) |
| MX (1) | MX2022012952A (ja) |
| PE (1) | PE20230388A1 (ja) |
| TW (1) | TW202202501A (ja) |
| WO (1) | WO2021211380A1 (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022069357A1 (en) * | 2020-10-01 | 2022-04-07 | Sandoz Ag | Crystalline form of selpercatinib |
| US20230183266A1 (en) | 2021-12-13 | 2023-06-15 | Loxo Oncology, Inc. | Crystalline forms of ret inhibitor and preparation thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI704148B (zh) * | 2016-10-10 | 2020-09-11 | 美商亞雷生物製藥股份有限公司 | 作為ｒｅｔ激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
| TWI783057B (zh) * | 2017-10-10 | 2022-11-11 | 美商絡速藥業公司 | 製備6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈的方法 |
| TWI812649B (zh) * | 2017-10-10 | 2023-08-21 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
| TWI791053B (zh) * | 2017-10-10 | 2023-02-01 | 美商亞雷生物製藥股份有限公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之結晶形式及其醫藥組合物 |
| EP3845531A4 (en) * | 2018-09-30 | 2021-11-24 | Applied Pharmaceutical Science, Inc. | SUBSTITUTED PYRAZOLE-CONDENSED RING DERIVATIVES, METHOD FOR THEIR PRODUCTION AND USE THEREOF |
| CN111004257B (zh) * | 2019-12-24 | 2021-06-29 | 武汉九州钰民医药科技有限公司 | 制备RET抑制剂Selpercatinib的方法 |
-
2021
- 2021-04-07 TW TW110112512A patent/TW202202501A/zh unknown
- 2021-04-09 EP EP21722702.4A patent/EP4136090A1/en active Pending
- 2021-04-09 PE PE2022002417A patent/PE20230388A1/es unknown
- 2021-04-09 KR KR1020227039684A patent/KR20230002706A/ko active Search and Examination
- 2021-04-09 MX MX2022012952A patent/MX2022012952A/es unknown
- 2021-04-09 JP JP2022562612A patent/JP2023522012A/ja active Pending
- 2021-04-09 CA CA3174316A patent/CA3174316A1/en active Pending
- 2021-04-09 CR CR20220520A patent/CR20220520A/es unknown
- 2021-04-09 IL IL297212A patent/IL297212A/en unknown
- 2021-04-09 BR BR112022020446A patent/BR112022020446A2/pt unknown
- 2021-04-09 AU AU2021255488A patent/AU2021255488A1/en active Pending
- 2021-04-09 WO PCT/US2021/026611 patent/WO2021211380A1/en active Application Filing
- 2021-04-09 CN CN202180043101.5A patent/CN115916791A/zh active Pending
-
2022
- 2022-10-14 CL CL2022002849A patent/CL2022002849A1/es unknown
- 2022-10-17 EC ECSENADI202280982A patent/ECSP22080982A/es unknown
- 2022-10-17 DO DO2022000221A patent/DOP2022000221A/es unknown
- 2022-10-19 CO CONC2022/0014882A patent/CO2022014882A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW202202501A (zh) | 2022-01-16 |
| BR112022020446A2 (pt) | 2022-11-29 |
| CR20220520A (es) | 2022-11-15 |
| CN115916791A (zh) | 2023-04-04 |
| CO2022014882A2 (es) | 2022-10-31 |
| DOP2022000221A (es) | 2023-01-15 |
| MX2022012952A (es) | 2023-01-11 |
| EP4136090A1 (en) | 2023-02-22 |
| JP2023522012A (ja) | 2023-05-26 |
| ECSP22080982A (es) | 2023-01-31 |
| PE20230388A1 (es) | 2023-03-06 |
| KR20230002706A (ko) | 2023-01-05 |
| CL2022002849A1 (es) | 2023-06-16 |
| IL297212A (en) | 2022-12-01 |
| WO2021211380A1 (en) | 2021-10-21 |
| AU2021255488A1 (en) | 2022-11-10 |
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