JP2021506787A5 - - Google Patents
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- Publication number
- JP2021506787A5 JP2021506787A5 JP2020532570A JP2020532570A JP2021506787A5 JP 2021506787 A5 JP2021506787 A5 JP 2021506787A5 JP 2020532570 A JP2020532570 A JP 2020532570A JP 2020532570 A JP2020532570 A JP 2020532570A JP 2021506787 A5 JP2021506787 A5 JP 2021506787A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- propionic acid
- bromo
- deuterium
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 91
- 229910052794 bromium Inorganic materials 0.000 claims 39
- 229910052801 chlorine Inorganic materials 0.000 claims 39
- 229910052731 fluorine Inorganic materials 0.000 claims 39
- 229910052740 iodine Inorganic materials 0.000 claims 39
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims 32
- 229910052805 deuterium Inorganic materials 0.000 claims 32
- 125000001424 substituent group Chemical group 0.000 claims 30
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 24
- 229910052722 tritium Inorganic materials 0.000 claims 24
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 20
- 125000003342 alkenyl group Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000000304 alkynyl group Chemical group 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- -1 n- propyl Chemical group 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- VAHKBLKSDJKDNN-AADKRJSRSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1C(C1)(Cl)Cl Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1C(C1)(Cl)Cl VAHKBLKSDJKDNN-AADKRJSRSA-N 0.000 claims 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 4
- 208000021642 Muscular disease Diseases 0.000 claims 3
- 201000009623 Myopathy Diseases 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 235000019260 propionic acid Nutrition 0.000 claims 3
- GIBPZNYNZVMVTR-VIFPVBQESA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1=CCCC1 Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1=CCCC1 GIBPZNYNZVMVTR-VIFPVBQESA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 206010028417 myasthenia gravis Diseases 0.000 claims 2
- 208000018360 neuromuscular disease Diseases 0.000 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- ZDNSZYZGSDMGRM-ZETCQYMHSA-N (2S)-2-(2-acetyl-4-chlorophenoxy)propanoic acid Chemical compound C(C)(=O)C1=C(O[C@H](C(=O)O)C)C=CC(=C1)Cl ZDNSZYZGSDMGRM-ZETCQYMHSA-N 0.000 claims 1
- DXKUKNNJHVQEMQ-VJBUCKLLSA-N (2S)-2-[4-chloro-2-(2,2-dideuteriopropanoyl)phenoxy]propanoic acid Chemical compound ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C(C(C)([2H])[2H])=O DXKUKNNJHVQEMQ-VJBUCKLLSA-N 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- XXGSZYKRTXPGNK-ZETCQYMHSA-N BrC1=C(O[C@H](C(=O)O)C)C(=CC(=C1)Br)CCOC Chemical compound BrC1=C(O[C@H](C(=O)O)C)C(=CC(=C1)Br)CCOC XXGSZYKRTXPGNK-ZETCQYMHSA-N 0.000 claims 1
- BEKICUWBRBNZGQ-ZDUSSCGKSA-N BrC1=CC(=C(O[C@H](C(=O)O)C(C)C)C=C1)C(CC)=O Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C(C)C)C=C1)C(CC)=O BEKICUWBRBNZGQ-ZDUSSCGKSA-N 0.000 claims 1
- ZEZKOPIJSPAIIR-ZETCQYMHSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C#C Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C#C ZEZKOPIJSPAIIR-ZETCQYMHSA-N 0.000 claims 1
- BRAOYMHRCSGGCP-ZETCQYMHSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C(CC)=O Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C(CC)=O BRAOYMHRCSGGCP-ZETCQYMHSA-N 0.000 claims 1
- QOFSMHGQQSTPEV-SILCLGDVSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1C(C1)COC Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1C(C1)COC QOFSMHGQQSTPEV-SILCLGDVSA-N 0.000 claims 1
- VNMPTUVWNJGIHA-BYDSUWOYSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1C(CC1)(F)F Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1C(CC1)(F)F VNMPTUVWNJGIHA-BYDSUWOYSA-N 0.000 claims 1
- SRHPRPVHOSVASN-ZETCQYMHSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1CC1 Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1CC1 SRHPRPVHOSVASN-ZETCQYMHSA-N 0.000 claims 1
- NZBIYRALPBBNCV-QMMMGPOBSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1CCC1 Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1CCC1 NZBIYRALPBBNCV-QMMMGPOBSA-N 0.000 claims 1
- UTZZPVLUZCSMQN-ZETCQYMHSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C=C Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C=C UTZZPVLUZCSMQN-ZETCQYMHSA-N 0.000 claims 1
- VKPLVJJOGJKMHQ-LURJTMIESA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C=C(F)F Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C=C(F)F VKPLVJJOGJKMHQ-LURJTMIESA-N 0.000 claims 1
- VGAWTMVLXWRCPY-QMMMGPOBSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)CCOC Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)CCOC VGAWTMVLXWRCPY-QMMMGPOBSA-N 0.000 claims 1
- QZKZRZCIBXXQMA-XKSSXDPKSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)[C@@H]1[C@H](C1)CO Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)[C@@H]1[C@H](C1)CO QZKZRZCIBXXQMA-XKSSXDPKSA-N 0.000 claims 1
- QZKZRZCIBXXQMA-OYNCUSHFSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)[C@H]1[C@@H](C1)CO Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)[C@H]1[C@@H](C1)CO QZKZRZCIBXXQMA-OYNCUSHFSA-N 0.000 claims 1
- OBSOUUUTKRRMPM-KPJROHGDSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)\C=C\Br Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)\C=C\Br OBSOUUUTKRRMPM-KPJROHGDSA-N 0.000 claims 1
- CKHAAWSUXUBMQO-KPJROHGDSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)\C=C\F Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1)\C=C\F CKHAAWSUXUBMQO-KPJROHGDSA-N 0.000 claims 1
- WBPPOCGUTDIUMD-LURJTMIESA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1F)C#C Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1F)C#C WBPPOCGUTDIUMD-LURJTMIESA-N 0.000 claims 1
- KWSDCYKAFKKWFK-LURJTMIESA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1F)C1CC1 Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1F)C1CC1 KWSDCYKAFKKWFK-LURJTMIESA-N 0.000 claims 1
- ZQAJZNKILLASDI-LURJTMIESA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1F)C=C Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1F)C=C ZQAJZNKILLASDI-LURJTMIESA-N 0.000 claims 1
- QKGOEXFNNSKUPQ-YFKPBYRVSA-N BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1F)C=C(F)F Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C)C=C1F)C=C(F)F QKGOEXFNNSKUPQ-YFKPBYRVSA-N 0.000 claims 1
- HALKUBBFBDKMNQ-ZDUSSCGKSA-N BrC1=CC(=C(O[C@H](C(=O)O)C2CCC2)C=C1)C#C Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)C2CCC2)C=C1)C#C HALKUBBFBDKMNQ-ZDUSSCGKSA-N 0.000 claims 1
- DHBSBASSODYVBS-JTQLQIEISA-N BrC1=CC(=C(O[C@H](C(=O)O)CC)C=C1)C#C Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)CC)C=C1)C#C DHBSBASSODYVBS-JTQLQIEISA-N 0.000 claims 1
- WVBVMYCVFSSQCO-NSHDSACASA-N BrC1=CC(=C(O[C@H](C(=O)O)CCF)C=C1)C#C Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)CCF)C=C1)C#C WVBVMYCVFSSQCO-NSHDSACASA-N 0.000 claims 1
- PRYSAUVJLCCVNL-LBPRGKRZSA-N BrC1=CC(=C(O[C@H](C(=O)O)CCF)C=C1)C1CC1 Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)CCF)C=C1)C1CC1 PRYSAUVJLCCVNL-LBPRGKRZSA-N 0.000 claims 1
- MXDSGXHKJJOVHP-NSHDSACASA-N BrC1=CC(=C(O[C@H](C(=O)O)CCF)C=C1)C=C Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)CCF)C=C1)C=C MXDSGXHKJJOVHP-NSHDSACASA-N 0.000 claims 1
- SUZRHQDQCKGYNW-LBPRGKRZSA-N BrC1=CC(=C(O[C@H](C(=O)O)CF)C=C1)C1CCC1 Chemical compound BrC1=CC(=C(O[C@H](C(=O)O)CF)C=C1)C1CCC1 SUZRHQDQCKGYNW-LBPRGKRZSA-N 0.000 claims 1
- YFQPZEJENXYPLO-AWEZNQCLSA-N BrC1=CC(=C(O[C@H](C(=O)OC)C(C)C)C=C1)C(CC)=O Chemical compound BrC1=CC(=C(O[C@H](C(=O)OC)C(C)C)C=C1)C(CC)=O YFQPZEJENXYPLO-AWEZNQCLSA-N 0.000 claims 1
- JOQDKMSZCWMFQE-LURJTMIESA-N C(C)(=O)C1=C(O[C@H](C(=O)O)C)C=C(C(=C1)Br)F Chemical compound C(C)(=O)C1=C(O[C@H](C(=O)O)C)C=C(C(=C1)Br)F JOQDKMSZCWMFQE-LURJTMIESA-N 0.000 claims 1
- RLGICSCEQHDLET-BELGNNRLSA-N C(C1=CC=CC=C1)OC1C(CC1)C1=C(O[C@H](C(=O)O)C)C=CC(=C1)Cl Chemical compound C(C1=CC=CC=C1)OC1C(CC1)C1=C(O[C@H](C(=O)O)C)C=CC(=C1)Cl RLGICSCEQHDLET-BELGNNRLSA-N 0.000 claims 1
- KIWFRNOBOWANRR-LURJTMIESA-N C1(CC1)C1=C(O[C@H](C(=O)O)C)C(=CC(=C1)F)F Chemical compound C1(CC1)C1=C(O[C@H](C(=O)O)C)C(=CC(=C1)F)F KIWFRNOBOWANRR-LURJTMIESA-N 0.000 claims 1
- OZHJSYXPZSSBHS-ZETCQYMHSA-N C1(CC1)C1=C(O[C@H](C(=O)O)C)C=CC(=C1)F Chemical compound C1(CC1)C1=C(O[C@H](C(=O)O)C)C=CC(=C1)F OZHJSYXPZSSBHS-ZETCQYMHSA-N 0.000 claims 1
- SLCPDGBVNQWFDT-QMMMGPOBSA-N C1(CCC1)C1=C(O[C@H](C(=O)O)C)C=CC(=C1)F Chemical compound C1(CCC1)C1=C(O[C@H](C(=O)O)C)C=CC(=C1)F SLCPDGBVNQWFDT-QMMMGPOBSA-N 0.000 claims 1
- 102100023457 Chloride channel protein 1 Human genes 0.000 claims 1
- 101710091665 Chloride channel protein 1 Proteins 0.000 claims 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 1
- XULKLTITWZQJGC-LURJTMIESA-N ClC1=CC(=C(O[C@H](C(=O)O)C)C(=C1)F)C1CC1 Chemical compound ClC1=CC(=C(O[C@H](C(=O)O)C)C(=C1)F)C1CC1 XULKLTITWZQJGC-LURJTMIESA-N 0.000 claims 1
- PBHWJGDNEJOMHD-ZETCQYMHSA-N ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C#C Chemical compound ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C#C PBHWJGDNEJOMHD-ZETCQYMHSA-N 0.000 claims 1
- DXKUKNNJHVQEMQ-ZETCQYMHSA-N ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C(CC)=O Chemical compound ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C(CC)=O DXKUKNNJHVQEMQ-ZETCQYMHSA-N 0.000 claims 1
- RHOUWXZQQABAAY-ZETCQYMHSA-N ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1CC1 Chemical compound ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1CC1 RHOUWXZQQABAAY-ZETCQYMHSA-N 0.000 claims 1
- RHQINRWDEFUSOV-QMMMGPOBSA-N ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1CCC1 Chemical compound ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C1CCC1 RHQINRWDEFUSOV-QMMMGPOBSA-N 0.000 claims 1
- QTBXPNQNRBYWIY-QRPNPIFTSA-N ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)CCC.[Na] Chemical compound ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)CCC.[Na] QTBXPNQNRBYWIY-QRPNPIFTSA-N 0.000 claims 1
- JMJUCHMWCKRWAX-KPJROHGDSA-N ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)\C=C\F Chemical compound ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1)\C=C\F JMJUCHMWCKRWAX-KPJROHGDSA-N 0.000 claims 1
- LQPQEHPHQVEWSA-LURJTMIESA-N ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1F)C#C Chemical compound ClC1=CC(=C(O[C@H](C(=O)O)C)C=C1F)C#C LQPQEHPHQVEWSA-LURJTMIESA-N 0.000 claims 1
- AGLNJCYYQSNWIX-JTQLQIEISA-N ClC1=CC(=C(O[C@H](C(=O)O)CF)C(=C1)F)C1CC1 Chemical compound ClC1=CC(=C(O[C@H](C(=O)O)CF)C(=C1)F)C1CC1 AGLNJCYYQSNWIX-JTQLQIEISA-N 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- MISLXJIXQZSEFC-LURJTMIESA-N FC1=C(O[C@H](C(=O)O)C)C(=CC(=C1)F)C(CC)=O Chemical compound FC1=C(O[C@H](C(=O)O)C)C(=CC(=C1)F)C(CC)=O MISLXJIXQZSEFC-LURJTMIESA-N 0.000 claims 1
- KQOJKBXEMWBVAN-ZETCQYMHSA-N FC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C(CC)=O Chemical compound FC1=CC(=C(O[C@H](C(=O)O)C)C=C1)C(CC)=O KQOJKBXEMWBVAN-ZETCQYMHSA-N 0.000 claims 1
- 102000004310 Ion Channels Human genes 0.000 claims 1
- 201000010743 Lambert-Eaton myasthenic syndrome Diseases 0.000 claims 1
- 206010028289 Muscle atrophy Diseases 0.000 claims 1
- 208000010366 Postpoliomyelitis syndrome Diseases 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 201000002342 diabetic polyneuropathy Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 201000010901 lateral sclerosis Diseases 0.000 claims 1
- 208000005264 motor neuron disease Diseases 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 230000020763 muscle atrophy Effects 0.000 claims 1
- 201000000585 muscular atrophy Diseases 0.000 claims 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 1
- 230000002232 neuromuscular Effects 0.000 claims 1
- 239000000842 neuromuscular blocking agent Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762598959P | 2017-12-14 | 2017-12-14 | |
| US62/598,959 | 2017-12-14 | ||
| EP18151651 | 2018-01-15 | ||
| EP18151651.9 | 2018-01-15 | ||
| PCT/EP2018/084988 WO2019115780A1 (en) | 2017-12-14 | 2018-12-14 | Phenoxy acids for the treatment of neuromuscular disorders |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2021506787A JP2021506787A (ja) | 2021-02-22 |
| JP2021506787A5 true JP2021506787A5 (https=) | 2021-12-16 |
| JP7287607B2 JP7287607B2 (ja) | 2023-06-06 |
| JP7287607B6 JP7287607B6 (ja) | 2024-02-19 |
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| BR112021025637A2 (pt) | 2019-06-19 | 2022-02-01 | Nmd Pharma As | Compostos para o tratamento de doenças neuromusculares |
| CN113072420B (zh) * | 2021-02-23 | 2022-05-20 | 中山大学 | 一类2-芳基取代的偕二氟环丁烷类化合物及其制备方法 |
| EP4731200A1 (en) | 2023-06-20 | 2026-04-29 | NMD Pharma A/S | Clc-1 inhibitors for use in the treatment of multiple sclerosis and neuromuscular diseases |
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| SE0301009D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| GB0409921D0 (en) | 2004-05-04 | 2004-06-09 | Novartis Ag | Organic compounds |
| GB0422057D0 (en) | 2004-10-05 | 2004-11-03 | Astrazeneca Ab | Novel compounds |
| EP2244711A4 (en) * | 2008-02-04 | 2011-08-24 | Cytokinetics Inc | CERTAIN CHEMICAL ENTITIES, COMPOSITIONS AND METHODS |
| JP6199991B2 (ja) * | 2013-01-18 | 2017-09-20 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ３置換ピラゾール及びｄｌｋ阻害剤としての使用 |
| MX389242B (es) * | 2015-06-15 | 2025-03-20 | Nmd Pharma As | Compuestos para su uso en el tratamiento de trastornos neuromusculares |
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- 2018-12-14 CN CN201880080805.8A patent/CN111491628B/zh active Active
- 2018-12-14 DK DK18816078.2T patent/DK3723746T3/da active
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- 2018-12-14 WO PCT/EP2018/084988 patent/WO2019115780A1/en not_active Ceased
- 2018-12-14 JP JP2020532570A patent/JP7287607B6/ja active Active
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