EA039607B1 - Бензодиазолиевые соединения в качестве ингибиторов enac - Google Patents

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Publication number

EA039607B1

EA039607B1 EA201991253A EA201991253A EA039607B1 EA 039607 B1 EA039607 B1 EA 039607B1 EA 201991253 A EA201991253 A EA 201991253A EA 201991253 A EA201991253 A EA 201991253A EA 039607 B1 EA039607 B1 EA 039607B1

Authority

EA

Eurasian Patent Office

Prior art keywords

amino

methyl

benzodiazol

pyrrolo

pyrazin

Prior art date

2016-11-22

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• 239000002713 epithelial sodium channel blocking agent Substances 0.000 title description 10
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 325
• 208000023504 respiratory system disease Diseases 0.000 claims abstract description 15
• 230000002265 prevention Effects 0.000 claims abstract description 11
• 102000003837 Epithelial Sodium Channels Human genes 0.000 claims abstract description 4
• 108090000140 Epithelial Sodium Channels Proteins 0.000 claims abstract description 4
• -1 chloro, methyl Chemical group 0.000 claims description 145
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 128
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
• 238000000034 method Methods 0.000 claims description 55
• 125000000217 alkyl group Chemical group 0.000 claims description 46
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 31
• 150000003839 salts Chemical class 0.000 claims description 31
• 229910052799 carbon Inorganic materials 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 230000001404 mediated effect Effects 0.000 claims description 21
• 150000001450 anions Chemical class 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 239000000843 powder Substances 0.000 claims description 19
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 230000007062 hydrolysis Effects 0.000 claims description 14
• 238000006460 hydrolysis reaction Methods 0.000 claims description 14
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 14
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 125000002947 alkylene group Chemical group 0.000 claims description 12
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 12
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 9
• 150000001768 cations Chemical class 0.000 claims description 9
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 8
• 201000010099 disease Diseases 0.000 claims description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 208000017520 skin disease Diseases 0.000 claims description 8
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 7
• 208000030533 eye disease Diseases 0.000 claims description 7
• 230000003993 interaction Effects 0.000 claims description 7
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 239000000443 aerosol Substances 0.000 claims description 5
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 238000006268 reductive amination reaction Methods 0.000 claims description 5
• 125000000134 2-(methylsulfanyl)ethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])[*] 0.000 claims description 4
• 150000003863 ammonium salts Chemical class 0.000 claims description 4
• 201000009267 bronchiectasis Diseases 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 230000009466 transformation Effects 0.000 claims description 4
• 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
• 206010006451 bronchitis Diseases 0.000 claims description 3
• 208000007451 chronic bronchitis Diseases 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• URVCBRGBGUUPJB-UHFFFAOYSA-O 3-amino-7-chloro-N-[(5-chloro-1,3-diethylbenzimidazol-1-ium-2-yl)methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCn1c(CNC(=O)c2nc3c(Cl)c[nH]c3nc2N)[n+](CC)c2ccc(Cl)cc12 URVCBRGBGUUPJB-UHFFFAOYSA-O 0.000 claims description 2
• QFRBQJKFGBJAFA-UHFFFAOYSA-O 3-amino-N-[(3-ethyl-5-methoxy-1-methylbenzimidazol-1-ium-2-yl)methyl]-6-methyl-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCn1c(CNC(=O)c2nc3cc(C)[nH]c3nc2N)[n+](C)c2ccc(OC)cc12 QFRBQJKFGBJAFA-UHFFFAOYSA-O 0.000 claims description 2
• MHCKYBXMHFAPDF-UOOXCUFBSA-O 3-amino-N-[[1,3-diethyl-5-[1-[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]piperidin-4-yl]benzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound NC1=C(N=C2C(=N1)NC=C2)C(=O)NCC1=[N+](C2=C(N1CC)C=C(C=C2)C1CCN(CC1)C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)CC MHCKYBXMHFAPDF-UOOXCUFBSA-O 0.000 claims description 2
• JYOLREURHCOLCB-UHFFFAOYSA-O 3-amino-N-[[1-benzyl-3-(2-oxo-2-piperidin-1-ylethyl)benzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound Nc1nc2[nH]ccc2nc1C(=O)NCc1n(CC(=O)N2CCCCC2)c2ccccc2[n+]1Cc1ccccc1 JYOLREURHCOLCB-UHFFFAOYSA-O 0.000 claims description 2
• VVPMGAABFXTBHV-UHFFFAOYSA-O 3-amino-N-[[3-ethyl-1-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]-5-methoxybenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](CCOCCOCCO)c2ccc(OC)cc12 VVPMGAABFXTBHV-UHFFFAOYSA-O 0.000 claims description 2
• VRUSXVQWIBYABT-UHFFFAOYSA-O 3-amino-N-[[3-ethyl-1-methyl-5-(trifluoromethoxy)benzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound C12=CC=C(C=C2N(C(=[N+]1C)CNC(=O)C1=NC2=C(NC=C2)N=C1N)CC)OC(F)(F)F VRUSXVQWIBYABT-UHFFFAOYSA-O 0.000 claims description 2
• IJYFYFZHUOCZPO-UHFFFAOYSA-O 3-amino-N-[[3-ethyl-1-methyl-5-(trifluoromethyl)benzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound [N+]=1(C2=C(N(C=1CNC(=O)C1=NC3=C(NC=C3)N=C1N)CC)C=C(C(F)(F)F)C=C2)C IJYFYFZHUOCZPO-UHFFFAOYSA-O 0.000 claims description 2
• MPIFEUWFQQAHPD-UHFFFAOYSA-O 3-amino-N-[[5-[2-(4-aminopiperidin-1-yl)ethylcarbamoyl]-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](CC)c2ccc(cc12)C(=O)NCCN1CCC(N)CC1 MPIFEUWFQQAHPD-UHFFFAOYSA-O 0.000 claims description 2
• RJSRSYSLBOQPFA-GORFEGJJSA-O 3-amino-N-[[5-[2-[bis[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]ethoxy]-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound NC1=C(N=C2C(=N1)NC=C2)C(=O)NCC1=[N+](C2=C(N1CC)C=CC(=C2)OCCN(C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)CC RJSRSYSLBOQPFA-GORFEGJJSA-O 0.000 claims description 2
• KDFILMISCGSFMY-GORFEGJJSA-O 3-amino-N-[[5-[2-[bis[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]ethylcarbamoyl]-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound NC1=C(N=C2C(=N1)NC=C2)C(=O)NCC1=[N+](C2=C(N1CC)C=C(C=C2)C(NCCN(C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)=O)CC KDFILMISCGSFMY-GORFEGJJSA-O 0.000 claims description 2
• FUKKRMYKMVJUHM-RGGGPRGCSA-O 3-amino-N-[[5-[3-[bis[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]propoxy]-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound NC1=C(N=C2C(=N1)NC=C2)C(=O)NCC1=[N+](C2=C(N1CC)C=CC(=C2)OCCCN(C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)CC FUKKRMYKMVJUHM-RGGGPRGCSA-O 0.000 claims description 2
• KLMDFMKURMQCRS-RGGGPRGCSA-O 3-amino-N-[[5-[3-[bis[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]propyl]-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound NC1=C(N=C2C(=N1)NC=C2)C(=O)NCC1=[N+](C2=C(N1CC)C=CC(=C2)CCCN(C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)CC KLMDFMKURMQCRS-RGGGPRGCSA-O 0.000 claims description 2
• PTNUKTMUMCUXEO-RGGGPRGCSA-O 3-amino-N-[[5-[3-[bis[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]propylcarbamoyl]-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound NC1=C(N=C2C(=N1)NC=C2)C(=O)NCC1=[N+](C2=C(N1CC)C=C(C=C2)C(NCCCN(C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)=O)CC PTNUKTMUMCUXEO-RGGGPRGCSA-O 0.000 claims description 2
• LYDVQYLLBNZMGL-GWJVXIDYSA-O 3-amino-N-[[5-[4-[bis[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]piperidine-1-carbonyl]-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCN1C(CNC(=O)C2=NC3=C(NC=C3)N=C2N)=[N+](CC)C2=CC=C(C=C12)C(=O)N1CCC(CC1)N(C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO LYDVQYLLBNZMGL-GWJVXIDYSA-O 0.000 claims description 2
• LMUWGXHPVNXDDW-YOANVILMSA-O 3-amino-N-[[5-[4-[bis[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]piperidine-1-carbonyl]-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]-7-bromo-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound NC1=C(N=C2C(=N1)NC=C2Br)C(=O)NCC1=[N+](C2=C(N1CC)C=C(C=C2)C(=O)N1CCC(CC1)N(C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)CC LMUWGXHPVNXDDW-YOANVILMSA-O 0.000 claims description 2
• XHJILJWUWLKTIU-YOANVILMSA-O 3-amino-N-[[5-[4-[bis[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]piperidine-1-carbonyl]-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]-7-chloro-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound NC1=C(N=C2C(=N1)NC=C2Cl)C(=O)NCC1=[N+](C2=C(N1CC)C=C(C=C2)C(=O)N1CCC(CC1)N(C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)CC XHJILJWUWLKTIU-YOANVILMSA-O 0.000 claims description 2
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
• ITFJTXUZGLDXMW-UHFFFAOYSA-N C(=O)[O-].NC1=C(N=C2C(=N1)NC=C2)C(=O)NCC2=[N+](C1=C(N2CC)C=C(C=C1)C(NCCCNC(=O)OC(C)(C)C)=O)CC Chemical compound C(=O)[O-].NC1=C(N=C2C(=N1)NC=C2)C(=O)NCC2=[N+](C1=C(N2CC)C=C(C=C1)C(NCCCNC(=O)OC(C)(C)C)=O)CC ITFJTXUZGLDXMW-UHFFFAOYSA-N 0.000 claims description 2
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
• 208000025678 Ciliary Motility disease Diseases 0.000 claims description 2
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 2
• 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 2
• 206010014561 Emphysema Diseases 0.000 claims description 2
• 201000004681 Psoriasis Diseases 0.000 claims description 2
• 208000006673 asthma Diseases 0.000 claims description 2
• 201000008937 atopic dermatitis Diseases 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 239000012634 fragment Substances 0.000 claims description 2
• 206010021198 ichthyosis Diseases 0.000 claims description 2
• 201000009266 primary ciliary dyskinesia Diseases 0.000 claims description 2
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
• 239000007921 spray Substances 0.000 claims description 2
• XKEPHCKAJKDUCN-UHFFFAOYSA-O tert-butyl 4-[2-[[(3-amino-5H-pyrrolo[2,3-b]pyrazine-2-carbonyl)amino]methyl]-1,3-diethylbenzimidazol-1-ium-5-yl]piperidine-1-carboxylate Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](CC)c2ccc(cc12)C1CCN(CC1)C(=O)OC(C)(C)C XKEPHCKAJKDUCN-UHFFFAOYSA-O 0.000 claims description 2
• CCLHPUMPIHMOQH-UHFFFAOYSA-O tert-butyl 4-[[2-[[(3-amino-5H-pyrrolo[2,3-b]pyrazine-2-carbonyl)amino]methyl]-1,3-diethylbenzimidazol-1-ium-5-carbonyl]amino]piperidine-1-carboxylate Chemical compound C(OC(=O)N1CCC(NC(=O)C2=CC3=C([N+](CC)=C(N3CC)CNC(=O)C3=NC4=C(NC=C4)N=C3N)C=C2)CC1)(C)(C)C CCLHPUMPIHMOQH-UHFFFAOYSA-O 0.000 claims description 2
• WLFXFLBFJLIOCE-UHFFFAOYSA-O tert-butyl N-[1-[2-[[(3-amino-5H-pyrrolo[2,3-b]pyrazine-2-carbonyl)amino]methyl]-1,3-diethylbenzimidazol-1-ium-5-carbonyl]piperidin-4-yl]carbamate Chemical compound C(OC(=O)NC1CCN(CC1)C(=O)C1=CC2=C([N+](CC)=C(N2CC)CNC(=O)C2=NC3=C(NC=C3)N=C2N)C=C1)(C)(C)C WLFXFLBFJLIOCE-UHFFFAOYSA-O 0.000 claims description 2
• PDMBIHGTNLAACY-UHFFFAOYSA-O tert-butyl N-[1-[2-[[2-[[(3-amino-5H-pyrrolo[2,3-b]pyrazine-2-carbonyl)amino]methyl]-1,3-diethylbenzimidazol-1-ium-5-carbonyl]amino]ethyl]piperidin-4-yl]carbamate Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](CC)c2ccc(cc12)C(=O)NCCN1CCC(CC1)NC(=O)OC(C)(C)C PDMBIHGTNLAACY-UHFFFAOYSA-O 0.000 claims description 2
• CKXUYLLRHJLNPZ-UHFFFAOYSA-O tert-butyl N-[2-[2-[[(3-amino-5H-pyrrolo[2,3-b]pyrazine-2-carbonyl)amino]methyl]-1,3-diethylbenzimidazol-1-ium-5-yl]oxyethyl]carbamate Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](CC)c2ccc(OCCNC(=O)OC(C)(C)C)cc12 CKXUYLLRHJLNPZ-UHFFFAOYSA-O 0.000 claims description 2
• OBELAVHRZYQCKJ-UHFFFAOYSA-O tert-butyl N-[3-[2-[[(3-amino-5H-pyrrolo[2,3-b]pyrazine-2-carbonyl)amino]methyl]-1,3-diethylbenzimidazol-1-ium-5-yl]oxypropyl]carbamate Chemical compound CC[N+]=1C2=C(N(C=1CNC(=O)C1=C(N)N=C3NC=CC3=N1)CC)C=C(OCCCNC(=O)OC(C)(C)C)C=C2 OBELAVHRZYQCKJ-UHFFFAOYSA-O 0.000 claims description 2
• OWDREPNQYVFFEL-UHFFFAOYSA-O tert-butyl N-[3-[2-[[(3-amino-5H-pyrrolo[2,3-b]pyrazine-2-carbonyl)amino]methyl]-1,3-diethylbenzimidazol-1-ium-5-yl]propyl]carbamate Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](CC)c2ccc(CCCNC(=O)OC(C)(C)C)cc12 OWDREPNQYVFFEL-UHFFFAOYSA-O 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims 4
• 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
• VGVNPVIJGFZPOP-UHFFFAOYSA-N 2-[2-[[(3-amino-5H-pyrrolo[2,3-b]pyrazine-2-carbonyl)amino]methyl]-3-ethyl-5-methoxybenzimidazol-1-ium-1-yl]acetate Chemical compound NC1=C(N=C2C(=N1)NC=C2)C(=O)NCC1=[N+](C2=C(N1CC)C=C(C=C2)OC)CC(=O)[O-] VGVNPVIJGFZPOP-UHFFFAOYSA-N 0.000 claims 1
• LKNBPCJQVGGYQT-FFDQPCAYSA-O 3-amino-N-[[1,3-diethyl-5-[1-[1-[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]piperidin-4-yl]pyrazol-4-yl]benzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound NC1=C(N=C2C(=N1)NC=C2)C(=O)NCC1=[N+](C2=C(N1CC)C=C(C=C2)C=1C=NN(C=1)C1CCN(CC1)C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)CC LKNBPCJQVGGYQT-FFDQPCAYSA-O 0.000 claims 1
• BGMWMUPICCKRCP-SWMUIXNUSA-O 3-amino-N-[[5-[(3R)-3-[bis[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]pyrrolidine-1-carbonyl]-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](CC)c2ccc(cc12)C(=O)N1CC[C@H](C1)N(C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO BGMWMUPICCKRCP-SWMUIXNUSA-O 0.000 claims 1
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