CA3174316A1 - Inhibiteur cristallin de ret - Google Patents
Inhibiteur cristallin de ret 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
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- 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
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- 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
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- 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
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- 150000000996 L-ascorbic acids Chemical class 0.000 claims description 3
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- 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
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- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
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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
Abstract
La présente invention concerne une forme cristalline de selpercatinib utile dans le traitement et la prévention de maladies qui peuvent être traitées avec un inhibiteur de kinase RET, y compris des maladies et des troubles associés à RET, et des procédés de production de cette forme cristalline.
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 (fr) | 2020-04-17 | 2021-04-09 | Inhibiteur cristallin de ret |
Publications (1)
Publication Number | Publication Date |
---|---|
CA3174316A1 true CA3174316A1 (fr) | 2021-10-21 |
Family
ID=75747118
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA3174316A Pending CA3174316A1 (fr) | 2020-04-17 | 2021-04-09 | Inhibiteur cristallin de ret |
Country Status (17)
Country | Link |
---|---|
EP (1) | EP4136090A1 (fr) |
JP (1) | JP2023522012A (fr) |
KR (1) | KR20230002706A (fr) |
CN (1) | CN115916791A (fr) |
AU (1) | AU2021255488A1 (fr) |
BR (1) | BR112022020446A2 (fr) |
CA (1) | CA3174316A1 (fr) |
CL (1) | CL2022002849A1 (fr) |
CO (1) | CO2022014882A2 (fr) |
CR (1) | CR20220520A (fr) |
DO (1) | DOP2022000221A (fr) |
EC (1) | ECSP22080982A (fr) |
IL (1) | IL297212A (fr) |
MX (1) | MX2022012952A (fr) |
PE (1) | PE20230388A1 (fr) |
TW (1) | TW202202501A (fr) |
WO (1) | WO2021211380A1 (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022069357A1 (fr) * | 2020-10-01 | 2022-04-07 | Sandoz Ag | Forme cristalline du selpercatinib |
WO2023114119A1 (fr) | 2021-12-13 | 2023-06-22 | Loxo Oncology, Inc. | Procédés de préparation de la forme cristalline a du selpercatinib, inhibiteur de ret |
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 |
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 |
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 |
EP3845531A4 (fr) * | 2018-09-30 | 2021-11-24 | Applied Pharmaceutical Science, Inc. | Dérivé cyclique condensé à un pyrazole substitué, son procédé de préparation et application associée |
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 BR BR112022020446A patent/BR112022020446A2/pt unknown
- 2021-04-09 CR CR20220520A patent/CR20220520A/es unknown
- 2021-04-09 CN CN202180043101.5A patent/CN115916791A/zh active Pending
- 2021-04-09 WO PCT/US2021/026611 patent/WO2021211380A1/fr active Application Filing
- 2021-04-09 AU AU2021255488A patent/AU2021255488A1/en active Pending
- 2021-04-09 PE PE2022002417A patent/PE20230388A1/es unknown
- 2021-04-09 EP EP21722702.4A patent/EP4136090A1/fr active Pending
- 2021-04-09 KR KR1020227039684A patent/KR20230002706A/ko active Search and Examination
- 2021-04-09 MX MX2022012952A patent/MX2022012952A/es unknown
- 2021-04-09 IL IL297212A patent/IL297212A/en unknown
- 2021-04-09 CA CA3174316A patent/CA3174316A1/fr active Pending
- 2021-04-09 JP JP2022562612A patent/JP2023522012A/ja 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 |
JP2023522012A (ja) | 2023-05-26 |
PE20230388A1 (es) | 2023-03-06 |
CN115916791A (zh) | 2023-04-04 |
DOP2022000221A (es) | 2023-01-15 |
CR20220520A (es) | 2022-11-15 |
CO2022014882A2 (es) | 2022-10-31 |
IL297212A (en) | 2022-12-01 |
KR20230002706A (ko) | 2023-01-05 |
MX2022012952A (es) | 2023-01-11 |
ECSP22080982A (es) | 2023-01-31 |
WO2021211380A1 (fr) | 2021-10-21 |
CL2022002849A1 (es) | 2023-06-16 |
AU2021255488A1 (en) | 2022-11-10 |
EP4136090A1 (fr) | 2023-02-22 |
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