JPWO2019246494A5 - - Google Patents
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- JPWO2019246494A5 JPWO2019246494A5 JP2020570965A JP2020570965A JPWO2019246494A5 JP WO2019246494 A5 JPWO2019246494 A5 JP WO2019246494A5 JP 2020570965 A JP2020570965 A JP 2020570965A JP 2020570965 A JP2020570965 A JP 2020570965A JP WO2019246494 A5 JPWO2019246494 A5 JP WO2019246494A5
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- JP
- Japan
- Prior art keywords
- cyp51a1
- inhibitor
- alkyl
- formula
- group
- Prior art date
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- 101710037807 CYP51A1 Proteins 0.000 claims description 107
- 102100007082 CYP51A1 Human genes 0.000 claims description 107
- 101710037876 CYP51G2 Proteins 0.000 claims description 107
- 239000003112 inhibitor Substances 0.000 claims description 102
- 230000002401 inhibitory effect Effects 0.000 claims description 102
- -1 triazimenol Chemical compound 0.000 claims description 81
- 102100002435 TARDBP Human genes 0.000 claims description 15
- 101710036241 TARDBP Proteins 0.000 claims description 15
- 208000009025 Nervous System Disease Diseases 0.000 claims description 14
- 206010029305 Neurological disorder Diseases 0.000 claims description 14
- 206010002026 Amyotrophic lateral sclerosis Diseases 0.000 claims description 10
- 206010028640 Myopathy Diseases 0.000 claims description 10
- 230000002776 aggregation Effects 0.000 claims description 10
- 238000004220 aggregation Methods 0.000 claims description 10
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- 230000035772 mutation Effects 0.000 claims description 7
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- 229920000160 (ribonucleotides)n+m Polymers 0.000 claims description 4
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- 208000003627 Muscular Dystrophy Diseases 0.000 claims description 4
- 208000010316 Myotonia Congenita Diseases 0.000 claims description 4
- 208000005392 Spasm Diseases 0.000 claims description 4
- 201000011474 congenital myopathy Diseases 0.000 claims description 4
- 230000002452 interceptive Effects 0.000 claims description 4
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- 239000004055 small Interfering RNA Substances 0.000 claims description 4
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 claims description 3
- VYNIUBZKEWJOJP-UNMCSNQZSA-N Azalanstat Chemical compound C1=CC(N)=CC=C1SC[C@H]1O[C@@](CCC=2C=CC(Cl)=CC=2)(CN2C=NC=C2)OC1 VYNIUBZKEWJOJP-UNMCSNQZSA-N 0.000 claims description 3
- 229950007234 Azalanstat Drugs 0.000 claims description 3
- 239000005822 Propiconazole Substances 0.000 claims description 3
- STJLVHWMYQXCPB-UHFFFAOYSA-N Propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 claims description 3
- 239000005825 Prothioconazole Substances 0.000 claims description 3
- 239000005839 Tebuconazole Substances 0.000 claims description 3
- PXMNMQRDXWABCY-UHFFFAOYSA-N Tebuconazole Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims description 3
- 230000003247 decreasing Effects 0.000 claims description 3
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 claims description 3
- 229960004740 voriconazole Drugs 0.000 claims description 3
- HHUQPWODPBDTLI-UHFFFAOYSA-N 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol Chemical group C1=NC=NN1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl HHUQPWODPBDTLI-UHFFFAOYSA-N 0.000 claims description 2
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 claims description 2
- VHVPQPYKVGDNFY-TUJWMRSMSA-N 2-[(2S)-butan-2-yl]-4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-TUJWMRSMSA-N 0.000 claims description 2
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- 206010013801 Duchenne muscular dystrophy Diseases 0.000 claims description 2
- RFHAOTPXVQNOHP-UHFFFAOYSA-N Fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 claims description 2
- 102100003780 GLRA1 Human genes 0.000 claims description 2
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- 206010053185 Glycogen storage disease type II Diseases 0.000 claims description 2
- KXDQPKMJSMCBEY-AEATXNOCSA-M Holothurin A Chemical compound [Na+].O[C@@H]1[C@@H](OC)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O[C@H]3[C@@H](OC[C@H]([C@@H]3O)OS([O-])(=O)=O)O[C@@H]3C([C@H]4[C@](C=5[C@H]([C@@]6(CC[C@]7(O)[C@](C)(C8OC(C)(C)CC8)OC(=O)[C@]76[C@@H](O)C=5)C)CC4)(C)CC3)(C)C)O[C@@H]2C)O)O[C@H](CO)[C@H]1O KXDQPKMJSMCBEY-AEATXNOCSA-M 0.000 claims description 2
- 201000001971 Huntington's disease Diseases 0.000 claims description 2
- 208000000209 Isaacs Syndrome Diseases 0.000 claims description 2
- XMAYWYJOQHXEEK-OZXSUGGESA-N Ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 claims description 2
- 208000009829 Lewy Body Disease Diseases 0.000 claims description 2
- 201000002832 Lewy body dementia Diseases 0.000 claims description 2
- 208000003393 Mammary Paget's Disease Diseases 0.000 claims description 2
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- 206010028289 Muscle atrophy Diseases 0.000 claims description 2
- 206010028334 Muscle spasms Diseases 0.000 claims description 2
- 206010028417 Myasthenia gravis Diseases 0.000 claims description 2
- 208000002086 Myofibrillar Myopathy Diseases 0.000 claims description 2
- 206010072359 Neuromyotonia Diseases 0.000 claims description 2
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- 206010061536 Parkinson's disease Diseases 0.000 claims description 2
- 208000001293 Peripheral Nervous System Disease Diseases 0.000 claims description 2
- 206010034606 Peripheral neuropathy Diseases 0.000 claims description 2
- 239000005820 Prochloraz Substances 0.000 claims description 2
- 229920001891 Small hairpin RNA Polymers 0.000 claims description 2
- 229920001985 Small interfering RNA Polymers 0.000 claims description 2
- 210000000278 Spinal Cord Anatomy 0.000 claims description 2
- 206010072148 Stiff person syndrome Diseases 0.000 claims description 2
- BWPGKXYWPBQBPV-MWQJAWBESA-N Theasaponin Chemical compound O([C@H]1[C@H](O)[C@H](O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@@H](O)CO1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)CO1)O)O[C@H]1CC[C@]2(C)[C@H]3CC=C4[C@@]([C@@]3(CC[C@H]2[C@@]1(CO)C)C)(C)C[C@@H](O)[C@@]1(CO)[C@@H](OC(C)=O)[C@@H](C(C[C@H]14)(C)C)OC(=O)C(\C)=C/C)C(O)=O)[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O BWPGKXYWPBQBPV-MWQJAWBESA-N 0.000 claims description 2
- BWPGKXYWPBQBPV-ZOADXXHESA-N Theasaponin Natural products O=C(O[C@@H]1[C@@H](OC(=O)C)[C@]2(CO)[C@@H](O)C[C@@]3(C)[C@@]4(C)[C@@H]([C@]5(C)[C@H]([C@@](CO)(C)[C@@H](O[C@@H]6[C@@H](O[C@@H]7[C@H](O[C@@H]8[C@@H](O)[C@H](O)[C@H](O)CO8)[C@H](O)[C@@H](O)CO7)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O7)[C@H](O)[C@@H](C(=O)O)O6)CC5)CC4)CC=C3[C@@H]2CC1(C)C)/C(=C/C)/C BWPGKXYWPBQBPV-ZOADXXHESA-N 0.000 claims description 2
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- 102000038129 antigens Human genes 0.000 claims description 2
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- 208000002395 autosomal recessive Spastic paraplegia 20 Diseases 0.000 claims description 2
- 230000003197 catalytic Effects 0.000 claims description 2
- 230000024881 catalytic activity Effects 0.000 claims description 2
- 230000002490 cerebral Effects 0.000 claims description 2
- 229960004022 clotrimazole Drugs 0.000 claims description 2
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 claims description 2
- 230000001054 cortical Effects 0.000 claims description 2
- 238000005538 encapsulation Methods 0.000 claims description 2
- 230000002255 enzymatic Effects 0.000 claims description 2
- 229960004884 fluconazole Drugs 0.000 claims description 2
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- 229920001239 microRNA Polymers 0.000 claims description 2
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- 201000002169 mitochondrial myopathy Diseases 0.000 claims description 2
- 230000020763 muscle atrophy Effects 0.000 claims description 2
- 201000000585 muscular atrophy Diseases 0.000 claims description 2
- RAGOYPUPXAKGKH-XAKZXMRKSA-N posaconazole Chemical compound O=C1N([C@H]([C@H](C)O)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@H]3C[C@@](CN4N=CN=C4)(OC3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 RAGOYPUPXAKGKH-XAKZXMRKSA-N 0.000 claims description 2
- 229960001589 posaconazole Drugs 0.000 claims description 2
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 claims description 2
- 230000000750 progressive Effects 0.000 claims description 2
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- 230000029058 respiratory gaseous exchange Effects 0.000 claims description 2
- 150000003384 small molecules Chemical group 0.000 claims description 2
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- 230000000638 stimulation Effects 0.000 claims description 2
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- 125000000217 alkyl group Chemical group 0.000 description 186
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 61
- 150000001875 compounds Chemical group 0.000 description 55
- 229910052739 hydrogen Inorganic materials 0.000 description 53
- 239000001257 hydrogen Substances 0.000 description 51
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 45
- 125000003545 alkoxy group Chemical group 0.000 description 42
- 125000005843 halogen group Chemical group 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 125000004432 carbon atoms Chemical group C* 0.000 description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 21
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- 125000003118 aryl group Chemical group 0.000 description 18
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- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 15
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- 125000000753 cycloalkyl group Chemical group 0.000 description 14
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- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 10
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
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- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 description 4
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- HCUOEKSZWPGJIM-IYNMRSRQSA-N (E,2Z)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N\O)\C(N)=O HCUOEKSZWPGJIM-IYNMRSRQSA-N 0.000 description 1
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 description 1
- PMOHNNYBSCQLEU-GHVLARLOSA-N 1-(6-bromopyridin-2-yl)-2-[[(2R)-2-(4-bromopyrimidin-2-yl)-2-hydroxyethyl]-[(2R)-1-[4-(2-ethoxyethoxy)phenyl]propan-2-yl]amino]ethanol Chemical compound C1=CC(OCCOCC)=CC=C1C[C@@H](C)N(C[C@@H](O)C=1N=C(Br)C=CN=1)CC(O)C1=CC=CC(Br)=N1 PMOHNNYBSCQLEU-GHVLARLOSA-N 0.000 description 1
- ZRJGUFKFWGXABF-NYRJJRHWSA-N 1-(6-chloropyridin-2-yl)-2-[[(2R)-1-[4-(2-ethoxyethoxy)phenyl]propan-2-yl]amino]ethanol Chemical compound C1=CC(OCCOCC)=CC=C1C[C@@H](C)NCC(O)C1=CC=CC(Cl)=N1 ZRJGUFKFWGXABF-NYRJJRHWSA-N 0.000 description 1
- 125000005987 1-oxo-thiomorpholinyl group Chemical group 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- CLVALLQETQTQMV-UHFFFAOYSA-N 2-(1,2,4-triazol-1-yl)ethanol Chemical compound OCCN1C=NC=N1 CLVALLQETQTQMV-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- AMSDWLOANMAILF-UHFFFAOYSA-N 2-imidazol-1-ylethanol Chemical compound OCCN1C=CN=C1 AMSDWLOANMAILF-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- GSSXLFACIJSBOM-UHFFFAOYSA-N 2H-pyran-2-ol Chemical compound OC1OC=CC=C1 GSSXLFACIJSBOM-UHFFFAOYSA-N 0.000 description 1
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000004946 alkenylalkyl group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000004350 aryl cycloalkyl group Chemical group 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 229960001274 fenticonazole Drugs 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
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- 125000004994 halo alkoxy alkyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 229940113083 morpholine Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
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| US62/688,115 | 2018-06-21 | ||
| PCT/US2019/038426 WO2019246494A1 (en) | 2018-06-21 | 2019-06-21 | Compositions and methods for the treatment and prevention of neurological disorders |
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| EP (1) | EP3810777A4 (de) |
| JP (1) | JP2021527693A (de) |
| KR (1) | KR20210040945A (de) |
| CN (1) | CN112805381A (de) |
| AU (1) | AU2019288677A1 (de) |
| BR (1) | BR112020025987A2 (de) |
| CA (1) | CA3104291A1 (de) |
| EA (1) | EA202190092A1 (de) |
| IL (1) | IL279634A (de) |
| MX (1) | MX2020014203A (de) |
| SG (1) | SG11202012706PA (de) |
| TW (1) | TW202017567A (de) |
| WO (1) | WO2019246494A1 (de) |
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| WO2021247893A1 (en) * | 2020-06-03 | 2021-12-09 | Yumanity Therapeutics, Inc. | Bicyclic heteroaromatic amide compounds and uses thereof |
| WO2021247910A1 (en) * | 2020-06-03 | 2021-12-09 | Yumanity Therapeutics, Inc. | Amino alcohol compounds and uses thereof |
| WO2021247916A1 (en) * | 2020-06-03 | 2021-12-09 | Yumanity Therapeutics, Inc. | Azetidine and spiroazetidine compounds and uses thereof |
| WO2023107630A2 (en) * | 2021-12-08 | 2023-06-15 | Kineta, Inc. | Amino alcohol compounds and uses thereof |
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-
2019
- 2019-06-21 EP EP19823565.7A patent/EP3810777A4/de not_active Withdrawn
- 2019-06-21 CN CN201980054373.8A patent/CN112805381A/zh active Pending
- 2019-06-21 CA CA3104291A patent/CA3104291A1/en active Pending
- 2019-06-21 WO PCT/US2019/038426 patent/WO2019246494A1/en active Application Filing
- 2019-06-21 MX MX2020014203A patent/MX2020014203A/es unknown
- 2019-06-21 TW TW108121819A patent/TW202017567A/zh unknown
- 2019-06-21 KR KR1020217001865A patent/KR20210040945A/ko active Search and Examination
- 2019-06-21 AU AU2019288677A patent/AU2019288677A1/en not_active Abandoned
- 2019-06-21 JP JP2020570965A patent/JP2021527693A/ja active Pending
- 2019-06-21 SG SG11202012706PA patent/SG11202012706PA/en unknown
- 2019-06-21 BR BR112020025987-0A patent/BR112020025987A2/pt unknown
- 2019-06-21 US US16/448,439 patent/US11241417B2/en active Active
- 2019-06-21 EA EA202190092A patent/EA202190092A1/ru unknown
-
2020
- 2020-12-21 IL IL279634A patent/IL279634A/en unknown
-
2021
- 2021-12-23 US US17/560,872 patent/US20220110920A1/en not_active Abandoned
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