JP2018510904A5 - - Google Patents
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- JP2018510904A5 JP2018510904A5 JP2017560888A JP2017560888A JP2018510904A5 JP 2018510904 A5 JP2018510904 A5 JP 2018510904A5 JP 2017560888 A JP2017560888 A JP 2017560888A JP 2017560888 A JP2017560888 A JP 2017560888A JP 2018510904 A5 JP2018510904 A5 JP 2018510904A5
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- JP
- Japan
- Prior art keywords
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- pharmaceutical composition
- composition according
- heterocycle
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 208000015439 Lysosomal storage disease Diseases 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 208000024720 Fabry Disease Diseases 0.000 claims description 2
- 208000010055 Globoid Cell Leukodystrophy Diseases 0.000 claims description 2
- 208000028226 Krabbe disease Diseases 0.000 claims description 2
- 208000026589 Wolman disease Diseases 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- -1 dimethylaminopropoxy group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 4
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- MZBVNYACSSGXID-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1-benzazepine Chemical group N1CCCCC2=CC=CC=C21 MZBVNYACSSGXID-UHFFFAOYSA-N 0.000 claims 2
- 208000032007 Glycogen storage disease due to acid maltase deficiency Diseases 0.000 claims 2
- 206010053185 Glycogen storage disease type II Diseases 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 201000004502 glycogen storage disease II Diseases 0.000 claims 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 208000025919 mucopolysaccharidosis type 7 Diseases 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- 208000001948 Farber Lipogranulomatosis Diseases 0.000 claims 1
- 208000033149 Farber disease Diseases 0.000 claims 1
- 208000015872 Gaucher disease Diseases 0.000 claims 1
- 102100033448 Lysosomal alpha-glucosidase Human genes 0.000 claims 1
- 208000002678 Mucopolysaccharidoses Diseases 0.000 claims 1
- 206010056893 Mucopolysaccharidosis VII Diseases 0.000 claims 1
- 201000001828 Sly syndrome Diseases 0.000 claims 1
- 208000010346 Sphingolipidoses Diseases 0.000 claims 1
- 201000001307 Sphingolipidosis Diseases 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 206010028093 mucopolysaccharidosis Diseases 0.000 claims 1
- 201000007633 neuronal ceroid lipofuscinosis 2 Diseases 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 239000000523 sample Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 108060001084 Luciferase Proteins 0.000 description 4
- 239000005089 Luciferase Substances 0.000 description 4
- 102000028677 Rab9 Human genes 0.000 description 4
- 108050007276 Rab9 Proteins 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003053 toxin Substances 0.000 description 3
- 231100000765 toxin Toxicity 0.000 description 3
- 108700012359 toxins Proteins 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 210000003712 lysosome Anatomy 0.000 description 2
- 230000001868 lysosomic effect Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DSSUHBJSDMHACJ-UHFFFAOYSA-N 2-methoxy-5-nitrobenzenesulfonyl chloride Chemical compound COC1=CC=C([N+]([O-])=O)C=C1S(Cl)(=O)=O DSSUHBJSDMHACJ-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- ZKUZSTXNVMIDCY-UHFFFAOYSA-N 4-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=NC=C1C(O)=O ZKUZSTXNVMIDCY-UHFFFAOYSA-N 0.000 description 1
- WNUKMPUZMALMLG-UHFFFAOYSA-N 5-amino-n-(4-bromophenyl)-2-methoxybenzenesulfonamide Chemical compound COC1=CC=C(N)C=C1S(=O)(=O)NC1=CC=C(Br)C=C1 WNUKMPUZMALMLG-UHFFFAOYSA-N 0.000 description 1
- 108010011170 Ala-Trp-Arg-His-Pro-Gln-Phe-Gly-Gly Proteins 0.000 description 1
- 102100026277 Alpha-galactosidase A Human genes 0.000 description 1
- 102220486220 Alpha-galactosidase A_N34S_mutation Human genes 0.000 description 1
- 208000031277 Amaurotic familial idiocy Diseases 0.000 description 1
- 108090000331 Firefly luciferases Proteins 0.000 description 1
- 101000933374 Gallus gallus Brain-specific homeobox/POU domain protein 3 Proteins 0.000 description 1
- 101000600434 Homo sapiens Putative uncharacterized protein encoded by MIR7-3HG Proteins 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 102100026001 Lysosomal acid lipase/cholesteryl ester hydrolase Human genes 0.000 description 1
- TTZOQOXARXTTRK-UHFFFAOYSA-N N-[3-[(4-bromophenyl)sulfamoyl]-4-methoxyphenyl]-4-methylpyridine-3-carboxamide Chemical compound COC1=C(C=C(NC(=O)C2=C(C)C=CN=C2)C=C1)S(=O)(=O)NC1=CC=C(Br)C=C1 TTZOQOXARXTTRK-UHFFFAOYSA-N 0.000 description 1
- 208000002537 Neuronal Ceroid-Lipofuscinoses Diseases 0.000 description 1
- BNUHAJGCKIQFGE-UHFFFAOYSA-N Nitroanisol Chemical compound COC1=CC=C([N+]([O-])=O)C=C1 BNUHAJGCKIQFGE-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102100037401 Putative uncharacterized protein encoded by MIR7-3HG Human genes 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 108700008625 Reporter Genes Proteins 0.000 description 1
- 108010017898 Shiga Toxins Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 108010055297 Sterol Esterase Proteins 0.000 description 1
- 108010090804 Streptavidin Proteins 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 108010030291 alpha-Galactosidase Proteins 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000001163 endosome Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- LEZNRPFLOGYEIO-QSEDPUOVSA-N ganglioside GT1b Chemical compound O[C@@H]1[C@@H](O)[C@H](OC[C@H](NC(=O)CCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@]2(O[C@H]([C@H](NC(C)=O)[C@@H](O)C2)[C@H](O)[C@@H](CO)O[C@]2(O[C@H]([C@H](NC(C)=O)[C@@H](O)C2)[C@H](O)[C@H](O)CO)C(O)=O)C(O)=O)[C@@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O[C@]4(O[C@H]([C@H](NC(C)=O)[C@@H](O)C4)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H](O)[C@@H](CO)O3)O)[C@@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](CO)O1 LEZNRPFLOGYEIO-QSEDPUOVSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000017476 juvenile neuronal ceroid lipofuscinosis Diseases 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 235000019626 lipase activity Nutrition 0.000 description 1
- 238000003468 luciferase reporter gene assay Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000002132 lysosomal effect Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 201000007607 neuronal ceroid lipofuscinosis 3 Diseases 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 108010044241 tetanus toxin fragment C Proteins 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562114840P | 2015-02-11 | 2015-02-11 | |
| US62/114,840 | 2015-02-11 | ||
| PCT/US2016/017504 WO2016130774A1 (en) | 2015-02-11 | 2016-02-11 | Benzenesulfonamide upregulators of npc1 for neimann-pick disease and other lysosomal storage disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018510904A JP2018510904A (ja) | 2018-04-19 |
| JP2018510904A5 true JP2018510904A5 (https=) | 2019-03-22 |
| JP6887389B2 JP6887389B2 (ja) | 2021-06-16 |
Family
ID=56614815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017560888A Active JP6887389B2 (ja) | 2015-02-11 | 2016-02-11 | ニーマン・ピック病および他のリソソーム蓄積障害のためのｎｐｃ１のベンゼンスルホンアミド上方制御剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10239830B2 (https=) |
| EP (1) | EP3256116B1 (https=) |
| JP (1) | JP6887389B2 (https=) |
| CN (1) | CN107949380B (https=) |
| AU (1) | AU2016219231B2 (https=) |
| CA (1) | CA2976449C (https=) |
| IL (2) | IL253896B (https=) |
| WO (1) | WO2016130774A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111289749B (zh) * | 2018-12-10 | 2023-04-14 | 北京蛋白质组研究中心 | C型1类尼曼-匹克蛋白检测物在制备筛查肝细胞癌产品中的应用 |
| WO2021150695A1 (en) * | 2020-01-22 | 2021-07-29 | Icahn School Of Medicine At Mount Sinai | Constrained n-substituted tetrahydrobenzoazepine sulfonamides as anticancer and neuroprotective agents |
| WO2022159566A1 (en) | 2021-01-21 | 2022-07-28 | Icahn School Of Medicine At Mount Sinai | Benzenesulfonamide agonists of trap1 for treating organ fibrosis |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6177447B1 (en) * | 1996-07-15 | 2001-01-23 | Universiteit Van Amsterdam | Deoxynojirimycin derivatives and their uses as glucosylceramidase inhibitors |
| CN1325385A (zh) * | 1998-11-09 | 2001-12-05 | 詹姆斯·布莱克基金有限公司 | 胃泌素和缩胆囊素受体配体 |
| WO2004035545A2 (en) * | 2002-10-18 | 2004-04-29 | E.I. Du Pont De Nemours And Company | Azolecarboxamide herbicides |
| RS56037B1 (sr) | 2004-06-24 | 2017-09-29 | Vertex Pharma | Modulatori atp-vezujućih kasetnih transportera |
| US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| CA2648202A1 (en) | 2006-04-11 | 2007-10-25 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of voltage-gated sodium channels |
| WO2013192165A2 (en) * | 2012-06-20 | 2013-12-27 | University Of Kansas | Compounds and methods for activating the apoptotic arm of the unfolded protein response |
| WO2014022841A1 (en) * | 2012-08-03 | 2014-02-06 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Cyclodextrin for the treatment of lysosomal storage diseases |
| US20140128352A1 (en) * | 2012-09-20 | 2014-05-08 | Buck Institute For Research On Aging | Compounds and methods for modulating mitochondrial metabolism and reactive oxygen species production |
| EP2823816A1 (en) * | 2013-07-09 | 2015-01-14 | Tragex Pharma | Inhibitors of Neuropilin and use thereof for the treatment of Neuropilin-related diseases |
-
2016
- 2016-02-11 AU AU2016219231A patent/AU2016219231B2/en active Active
- 2016-02-11 EP EP16749864.1A patent/EP3256116B1/en active Active
- 2016-02-11 CA CA2976449A patent/CA2976449C/en active Active
- 2016-02-11 CN CN201680020467.XA patent/CN107949380B/zh active Active
- 2016-02-11 WO PCT/US2016/017504 patent/WO2016130774A1/en not_active Ceased
- 2016-02-11 US US15/549,743 patent/US10239830B2/en active Active
- 2016-02-11 JP JP2017560888A patent/JP6887389B2/ja active Active
-
2017
- 2017-08-08 IL IL253896A patent/IL253896B/en active IP Right Grant
-
2019
- 2019-08-21 IL IL26881119A patent/IL268811A/en unknown
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