JP2020504753A5 - - Google Patents
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- Publication number
- JP2020504753A5 JP2020504753A5 JP2019535368A JP2019535368A JP2020504753A5 JP 2020504753 A5 JP2020504753 A5 JP 2020504753A5 JP 2019535368 A JP2019535368 A JP 2019535368A JP 2019535368 A JP2019535368 A JP 2019535368A JP 2020504753 A5 JP2020504753 A5 JP 2020504753A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- sulfonamide
- indole
- fluoro
- unsubstituted
- 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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- -1 chloro, bromo, iodo Chemical group 0.000 claims description 490
- 125000003545 alkoxy group Chemical group 0.000 claims description 272
- 125000001153 fluoro group Chemical group F* 0.000 claims description 244
- 229910052739 hydrogen Inorganic materials 0.000 claims description 234
- 239000001257 hydrogen Substances 0.000 claims description 234
- 125000000217 alkyl group Chemical group 0.000 claims description 186
- 150000002431 hydrogen Chemical group 0.000 claims description 153
- 229910052736 halogen Chemical group 0.000 claims description 119
- 150000002367 halogens Chemical group 0.000 claims description 114
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 93
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 87
- 150000001875 compounds Chemical class 0.000 claims description 72
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 67
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000003342 alkenyl group Chemical group 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 125000000304 alkynyl group Chemical group 0.000 claims description 46
- 125000001246 bromo group Chemical group Br* 0.000 claims description 43
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 35
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 35
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000012453 solvate Substances 0.000 claims description 34
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 33
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000004076 pyridyl group Chemical group 0.000 claims description 30
- 239000013078 crystal Substances 0.000 claims description 29
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 28
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 28
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 claims description 15
- 208000016192 Demyelinating disease Diseases 0.000 claims description 15
- 206010012305 Demyelination Diseases 0.000 claims description 15
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 208000035475 disorder Diseases 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 13
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims description 11
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 11
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 11
- 208000011580 syndromic disease Diseases 0.000 claims description 11
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 10
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 10
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 201000006417 multiple sclerosis Diseases 0.000 claims description 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 10
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 8
- AWBOSXFRPFZLOP-UHFFFAOYSA-N 2,1,3-benzoxadiazole Chemical compound C1=CC=CC2=NON=C21 AWBOSXFRPFZLOP-UHFFFAOYSA-N 0.000 claims description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
- 230000023105 myelination Effects 0.000 claims description 7
- FTNJQNQLEGKTGD-ZFJHNFROSA-N 1,3-benzodioxole Chemical group C1O[13C]=2[13CH]=[13CH][13CH]=[13CH][13C]=2O1 FTNJQNQLEGKTGD-ZFJHNFROSA-N 0.000 claims description 6
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 6
- 208000032194 Acute haemorrhagic leukoencephalitis Diseases 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 102000014461 Ataxins Human genes 0.000 claims description 6
- 108010078286 Ataxins Proteins 0.000 claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 6
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims description 6
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims description 6
- 150000001540 azides Chemical class 0.000 claims description 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 210000005013 brain tissue Anatomy 0.000 claims description 6
- 208000009885 central pontine myelinolysis Diseases 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical compound C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000006005 fluoroethoxy group Chemical group 0.000 claims description 4
- 230000002093 peripheral effect Effects 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 3
- 208000020925 Bipolar disease Diseases 0.000 claims description 3
- 208000014644 Brain disease Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 208000010693 Charcot-Marie-Tooth Disease Diseases 0.000 claims description 3
- 206010010252 Concentric sclerosis Diseases 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 claims description 3
- 206010049020 Encephalitis periaxialis diffusa Diseases 0.000 claims description 3
- 208000032274 Encephalopathy Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 206010021143 Hypoxia Diseases 0.000 claims description 3
- 208000001089 Multiple system atrophy Diseases 0.000 claims description 3
- 208000003435 Optic Neuritis Diseases 0.000 claims description 3
- 206010069350 Osmotic demyelination syndrome Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 208000021235 Schilder disease Diseases 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 208000002552 acute disseminated encephalomyelitis Diseases 0.000 claims description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 230000007954 hypoxia Effects 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 208000008795 neuromyelitis optica Diseases 0.000 claims description 3
- 230000009984 peri-natal effect Effects 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 230000000306 recurrent effect Effects 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 230000000451 tissue damage Effects 0.000 claims description 3
- 231100000827 tissue damage Toxicity 0.000 claims description 3
- 208000037816 tissue injury Diseases 0.000 claims description 3
- 239000003053 toxin Substances 0.000 claims description 3
- 231100000765 toxin Toxicity 0.000 claims description 3
- 108700012359 toxins Proteins 0.000 claims description 3
- 230000000472 traumatic effect Effects 0.000 claims description 3
- 210000004885 white matter Anatomy 0.000 claims description 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- 150000000183 1,3-benzoxazoles Chemical class 0.000 claims description 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 2
- XJVDIMLQFRPIMP-UHFFFAOYSA-N 3-methyl-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(C)OC(=O)C2=C1 XJVDIMLQFRPIMP-UHFFFAOYSA-N 0.000 claims description 2
- NBTPVYAEZALYIJ-UHFFFAOYSA-N 5-bromo-6-chloro-N-(4-chloro-2,5-difluorophenyl)-1H-indole-3-sulfonamide Chemical compound BrC=1C=C2C(=CNC2=CC=1Cl)S(=O)(=O)NC1=C(C=C(C(=C1)F)Cl)F NBTPVYAEZALYIJ-UHFFFAOYSA-N 0.000 claims description 2
- AYLDUKSYEVZYRT-UHFFFAOYSA-N 6-bromo-N-(2,4-difluorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-sulfonamide N-(2,2-difluoro-1,3-benzodioxol-4-yl)-6-methylsulfonyl-1H-indole-3-sulfonamide Chemical compound BrC1=CC=C2C(=N1)NC=C2S(=O)(=O)NC2=C(C=C(C=C2)F)F.FC2(OC1=C(O2)C=CC=C1NS(=O)(=O)C1=CNC2=CC(=CC=C12)S(=O)(=O)C)F AYLDUKSYEVZYRT-UHFFFAOYSA-N 0.000 claims description 2
- UPKPNIFYJDQRBL-UHFFFAOYSA-N 6-bromo-N-(4-cyanophenyl)-1H-indole-3-sulfonamide 6-chloro-N-(4-chloro-2,5-difluorophenyl)-7-(2,2-difluoroethoxy)-1H-indole-3-sulfonamide Chemical compound BrC1=CC=C2C(=CNC2=C1)S(=O)(=O)NC1=CC=C(C=C1)C#N.ClC1=CC=C2C(=CNC2=C1OCC(F)F)S(=O)(=O)NC1=C(C=C(C(=C1)F)Cl)F UPKPNIFYJDQRBL-UHFFFAOYSA-N 0.000 claims description 2
- RCVMTDVQQGOWNZ-UHFFFAOYSA-N 6-chloro-N-(2,4,5-trifluorophenyl)-1H-indole-3-sulfonamide N-[4-(difluoromethoxy)-2,5-difluorophenyl]-6-methylsulfinyl-1H-indole-3-sulfonamide Chemical compound Fc1cc(F)c(NS(=O)(=O)c2c[nH]c3cc(Cl)ccc23)cc1F.CS(=O)c1ccc2c(c[nH]c2c1)S(=O)(=O)Nc1cc(F)c(OC(F)F)cc1F RCVMTDVQQGOWNZ-UHFFFAOYSA-N 0.000 claims description 2
- JUGTZHMQUVPXOS-UHFFFAOYSA-N 6-chloro-N-(2,5-difluoro-4-methylphenyl)-1H-pyrrolo[2,3-b]pyridine-3-sulfonamide N-(4-chloro-2,5-difluorophenyl)-8-oxo-1,9-dihydropyrrolo[3,2-h]quinoline-3-sulfonamide Chemical compound Cc1cc(F)c(NS(=O)(=O)c2c[nH]c3nc(Cl)ccc23)cc1F.Fc1cc(NS(=O)(=O)c2c[nH]c3c2ccc2ccc(=O)[nH]c32)c(F)cc1Cl JUGTZHMQUVPXOS-UHFFFAOYSA-N 0.000 claims description 2
- WEJKSGPVXNCTFP-UHFFFAOYSA-N 6-chloro-N-(4,6-dichloropyridin-2-yl)-1H-indole-3-sulfonamide N-(2,2-difluoro-1,3-benzodioxol-4-yl)-5-iodo-1H-pyrrolo[2,3-b]pyridine-3-sulfonamide Chemical compound ClC1=CC=C2C(=CNC2=C1)S(=O)(=O)NC1=NC(=CC(=C1)Cl)Cl.FC1(OC2=C(O1)C=CC=C2NS(=O)(=O)C2=CNC1=NC=C(C=C12)I)F WEJKSGPVXNCTFP-UHFFFAOYSA-N 0.000 claims description 2
- KMAGLOZKFZXCKJ-UHFFFAOYSA-N 6-chloro-N-(4-chloro-2,5-difluorophenyl)-1H-indole-3-sulfonamide 6-chloro-N-[4-(difluoromethoxy)-2,5-difluorophenyl]-1H-indole-3-sulfonamide Chemical compound ClC1=CC=C2C(=CNC2=C1)S(=O)(=O)NC1=C(C=C(C(=C1)F)OC(F)F)F.ClC1=CC=C2C(=CNC2=C1)S(=O)(=O)NC1=C(C=C(C(=C1)F)Cl)F KMAGLOZKFZXCKJ-UHFFFAOYSA-N 0.000 claims description 2
- PCPSTIWCSWWMHI-UHFFFAOYSA-N 6-chloro-N-(4-chloro-2,5-difluorophenyl)-7-methylsulfinyl-1H-indole-3-sulfonamide 6-chloro-N-(3,6-difluoro-5-propan-2-ylpyridin-2-yl)-1H-indole-3-sulfonamide Chemical compound CC(C)c1cc(F)c(NS(=O)(=O)c2c[nH]c3cc(Cl)ccc23)nc1F.CS(=O)c1c(Cl)ccc2c(c[nH]c12)S(=O)(=O)Nc1cc(F)c(Cl)cc1F PCPSTIWCSWWMHI-UHFFFAOYSA-N 0.000 claims description 2
- UONNBAGIVWWWEA-UHFFFAOYSA-N 6-chloro-N-(6-cyano-2,2-difluoro-1,3-benzodioxol-4-yl)-1H-indole-3-sulfonamide N-(4-chloro-2,5-difluorophenyl)-2-fluoro-6-methoxy-1H-indole-3-sulfonamide Chemical compound ClC1=CC(=C(C=C1F)NS(=O)(=O)C1=C(NC2=CC(=CC=C12)OC)F)F.ClC1=CC=C2C(=CNC2=C1)S(=O)(=O)NC1=CC(=CC=2OC(OC21)(F)F)C#N UONNBAGIVWWWEA-UHFFFAOYSA-N 0.000 claims description 2
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- GWNPPHYEJITOHT-UHFFFAOYSA-N methanesulfinyl fluoride Chemical compound CS(F)=O GWNPPHYEJITOHT-UHFFFAOYSA-N 0.000 description 2
- KNWQLFOXPQZGPX-UHFFFAOYSA-N methanesulfonyl fluoride Chemical compound CS(F)(=O)=O KNWQLFOXPQZGPX-UHFFFAOYSA-N 0.000 description 2
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| WO2018119142A1 (en) | 2016-12-21 | 2018-06-28 | Amgen Inc. | Anti-tnf alpha antibody formulations |
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| US11708376B2 (en) * | 2018-04-20 | 2023-07-25 | Virginia Tech Intellectual Properties, Inc. | Substituted imidazo[4,5-b]pyridines, imidazo[4,5-b]pyrazines, and oxazolo[4,5- b]pyrazines as mitochondrial uncouplers |
| TWI857957B (zh) * | 2018-06-19 | 2024-10-11 | 德商Ｕｃｂ製藥有限公司 | 吡啶基及吡基-（氮）吲哚磺醯胺 |
| EP3584244A1 (en) * | 2018-06-20 | 2019-12-25 | UCB Pharma GmbH | Substituted alkoxypyridinyl indolsulfonamides |
| EP3847154A1 (en) * | 2018-09-03 | 2021-07-14 | F. Hoffmann-La Roche AG | Carboxamide and sulfonamide derivatives useful as tead modulators |
| CN110128422B (zh) * | 2019-01-04 | 2022-03-18 | 金凯(辽宁)生命科技股份有限公司 | 5-甲氧基-7-氮杂吲哚的合成方法 |
| JP2022517797A (ja) * | 2019-01-17 | 2022-03-10 | アイエフエム デュー インコーポレイテッド | Ｓｔｉｎｇ活性に関連する状態を治療するための化合物および組成物 |
| GB201903671D0 (en) * | 2019-03-18 | 2019-05-01 | Univ Edinburgh | Small molecule photosensitizers for photodynamic therapy |
| WO2020254289A1 (en) | 2019-06-17 | 2020-12-24 | Ucb Pharma Gmbh | N-(phenyl)-indole-3-sulfonamide derivatives and related compounds as gpr17 modulators for treating cns disorders such as multiple sclerosis |
| US20230167406A1 (en) * | 2020-05-01 | 2023-06-01 | The Children's Medical Center Corporation | Compositions and methods of promoting myelination |
| CN112375027B (zh) * | 2020-12-07 | 2023-03-31 | 中国药科大学 | 吲哚磺酰胺类衍生物及其医药用途 |
| CN112266328B (zh) * | 2020-12-09 | 2023-11-03 | 郑州萃智医药科技有限公司 | 3-氟-4-硝基苯甲醛的合成路线及制备方法 |
| JP2024507176A (ja) | 2021-02-26 | 2024-02-16 | エフ． ホフマン－ラ ロシュ アーゲー | 新規なピリミジン－２－イルスルホンアミド誘導体 |
| WO2022254027A1 (en) * | 2021-06-04 | 2022-12-08 | Rewind Therapeutics Nv | 3-pyrrolylsulfonamide compounds as gpr17 antagonists |
| IL310724A (en) | 2021-08-10 | 2024-04-01 | Ifm Due Inc | COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF CONDITIONS ASSOCIATED WITH STING ACTIVITY |
| CN114276319B (zh) * | 2022-01-06 | 2023-11-03 | 滁州学院 | 一种劳拉替尼中间体的合成方法 |
| CN114315741B (zh) * | 2022-01-19 | 2023-09-12 | 贵州医科大学 | 一种硫代化合物及其制备方法与应用 |
| JP2025523939A (ja) | 2022-07-20 | 2025-07-25 | エフ． ホフマン－ラ ロシュ アーゲー | 新規のナフチルおよびイソキノリンスルホンアミド誘導体 |
| US20260028335A1 (en) | 2022-07-20 | 2026-01-29 | Hoffmann-La Roche Inc. | Novel isothiazol-3-yl and isoxazol-3-yl sulfonamide compounds |
| CN119546576A (zh) | 2022-07-20 | 2025-02-28 | 豪夫迈·罗氏有限公司 | 新颖的异喹啉酮、吡咯并吡啶酮和噻吩并吡啶酮磺酰胺衍生物 |
| EP4558496A1 (en) | 2022-07-20 | 2025-05-28 | F. Hoffmann-La Roche AG | Novel pyrimidinyl and triazinyl sulfonamide derivatives |
| WO2024017857A1 (en) * | 2022-07-20 | 2024-01-25 | F. Hoffmann-La Roche Ag | Novel imidazopyridine and pyrazolopyridine sulfonamide derivatives |
| KR20250121546A (ko) * | 2022-11-20 | 2025-08-12 | 마이로발란 테라퓨틱스, 인크. | Gpr17 조절제 및 이의 용도 |
| AR131263A1 (es) * | 2022-12-02 | 2025-03-05 | Rewind Therapeutics Nv | Compuestos de pirrolil-sulfonamida fusionados |
| WO2024153233A1 (en) * | 2023-01-19 | 2024-07-25 | Nanjing Immunophage Biotech Co., Ltd | Compounds and their uses as gpr17 antagonists |
| CN116947879B (zh) * | 2023-07-25 | 2025-10-31 | 沈阳药科大学 | 一种bbi608类衍生物及其制备方法和在制备治疗stat3介导疾病的药物中的应用 |
| WO2025038863A1 (en) * | 2023-08-15 | 2025-02-20 | Biogen Ma Inc. | Indole and pyrroloypyridine derivatives as gpr17 modulators |
| WO2025195241A1 (zh) * | 2024-03-19 | 2025-09-25 | 迈巴制药(南京)有限公司 | Gpr17受体抑制剂及其用途 |
| GB2701173A (en) | 2024-05-23 | 2026-04-22 | Pheno Therapeutics Ltd | Compounds |
| GB2700773A (en) | 2024-05-23 | 2026-03-11 | Pheno Therapeutics Ltd | Compounds |
| GB2642355A (en) * | 2024-07-05 | 2026-01-07 | Pheno Therapeutics Ltd | Polymorphs |
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| DE19814084B4 (de) | 1998-03-30 | 2005-12-22 | Lts Lohmann Therapie-Systeme Ag | D2-Agonist enthaltendes transdermales therapeutisches System zur Behandlung des Parkinson-Syndroms und Verfahren zu seiner Herstellung |
| NZ514453A (en) * | 1999-02-26 | 2003-04-29 | Merck & Co Inc | Novel sulfonamide compounds and uses thereof |
| US6521658B1 (en) * | 1999-05-28 | 2003-02-18 | Abbott Laboratories | Cell proliferation inhibitors |
| SE9904750D0 (sv) | 1999-12-23 | 1999-12-23 | Pharmacia & Upjohn Ab | New formulation, use and method |
| EP1406884A1 (en) * | 2001-05-11 | 2004-04-14 | Biovitrum Ab | Arylsusfonamide compounds for the treatment of obesity, type ii diabetes and cns-disorders |
| SE0102048D0 (sv) * | 2001-06-11 | 2001-06-11 | Pharmacia Ab | New Compounds |
| DE602005024537D1 (de) | 2004-04-27 | 2010-12-16 | Takeda Pharmaceutical | Neuer ligand eines g-protein-konjugierten rezeptorproteins und verwendung davon |
| ITMI20042007A1 (it) | 2004-10-21 | 2005-01-21 | Consiglio Nazionale Ricerche | "modulatori del ricettore gpr17 e loro impieghi terapeutici" |
| WO2009000262A1 (de) | 2007-06-25 | 2008-12-31 | Acino Ag | Elektrophoretisches transdermales applikationssystem |
| EP2240474B1 (en) * | 2007-12-26 | 2012-03-14 | Sanofi | Cyclic pyridyl-n-(1,3,4)-thiadiazol-2-yl-benzene sulfonamides, processes for their preparation and their use as pharmaceuticals |
| US8318725B2 (en) * | 2008-09-17 | 2012-11-27 | Suven Life Sciences Limited | Aryl indolyl sulfonamide compounds and their use as 5-HT6 ligands |
| WO2010126002A1 (ja) * | 2009-04-28 | 2010-11-04 | 塩野義製薬株式会社 | ヘテロ環スルホンアミド化合物を含有する医薬 |
| GB2491520A (en) | 2010-03-11 | 2012-12-05 | Jerry Swinford | Method and apparatus for washing downhole tubulars and equipment |
| EP2567698B1 (en) | 2011-09-07 | 2014-02-12 | Rheinische Friedrich-Wilhelms-Universität Bonn | GPR 17 agonists and screening assay |
| KR20150008468A (ko) * | 2012-05-09 | 2015-01-22 | 폰다지오네 이탈리아나 스클레로시 멀티플라 - 에프아이에스엠 온러스 | Gpr17 수용체 조절제 |
| RU2519546C1 (ru) * | 2013-01-16 | 2014-06-10 | Общество С Ограниченной Ответственностью "Биоинтегратор" (Ооо "Биоинтегратор") | КОНЪЮГАТЫ И МАЛЫЕ МОЛЕКУЛЫ, ВЗАИМОДЕЙСТВУЮЩИЕ С РЕЦЕПТОРОМ CD16а |
| EP2997966A1 (en) * | 2014-09-16 | 2016-03-23 | Sanofi | Naphthyl Sulfonamide Pyrrolidine Derivatives as KEAP-1 Modulators for the Treatment of Diabetes, Obesity, Dyslipidemia and Related Disorders |
| EP2998294A1 (en) * | 2014-09-16 | 2016-03-23 | Sanofi | Naphthyl sulfonamide phenyl derivatives as KEAP-1 modulators for the treatment of diabetes, obesity, dyslipidemia and related disorders |
| WO2016089062A2 (en) * | 2014-12-02 | 2016-06-09 | C&C Research Laboratories | Heterocyclic derivatives and use thereof |
| ES2856125T3 (es) * | 2016-02-05 | 2021-09-27 | Ea Pharma Co Ltd | Derivado de sulfonamida y composición farmacéutica que contiene la misma |
| TWI754702B (zh) * | 2016-12-28 | 2022-02-11 | 德商Ｕｃｂ製藥有限公司 | （氮雜）吲哚－和苯並呋喃－３－磺醯胺類 |
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