CA3043132A1 - Benzodiazolium compounds as enac inhibitors - Google Patents

Info

Publication number

CA3043132A1

CA3043132A1 CA3043132A CA3043132A CA3043132A1 CA 3043132 A1 CA3043132 A1 CA 3043132A1 CA 3043132 A CA3043132 A CA 3043132A CA 3043132 A CA3043132 A CA 3043132A CA 3043132 A1 CA3043132 A1 CA 3043132A1

Authority

CA

Canada

Prior art keywords

amino

methyl

benzodiazol

ium

pyrrolo

Prior art date

2016-11-22

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.)

Pending

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000002713 epithelial sodium channel blocking agent Substances 0.000 title description 11
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 367
• 238000011282 treatment Methods 0.000 claims abstract description 30
• 208000023504 respiratory system disease Diseases 0.000 claims abstract description 18
• 230000002265 prevention Effects 0.000 claims abstract description 5
• 238000006243 chemical reaction Methods 0.000 claims description 170
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 117
• -1 chloro, methyl Chemical group 0.000 claims description 104
• 125000000217 alkyl group Chemical group 0.000 claims description 63
• 229910052757 nitrogen Inorganic materials 0.000 claims description 59
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
• 238000000034 method Methods 0.000 claims description 52
• 125000005843 halogen group Chemical group 0.000 claims description 43
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 43
• 125000000623 heterocyclic group Chemical group 0.000 claims description 42
• 125000002947 alkylene group Chemical group 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 150000001450 anions Chemical class 0.000 claims description 20
• 125000003118 aryl group Chemical group 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 238000002360 preparation method Methods 0.000 claims description 18
• 239000000843 powder Substances 0.000 claims description 17
• 230000007062 hydrolysis Effects 0.000 claims description 16
• 238000006460 hydrolysis reaction Methods 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 239000013543 active substance Substances 0.000 claims description 15
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 15
• 125000001475 halogen functional group Chemical group 0.000 claims description 13
• 230000008569 process Effects 0.000 claims description 13
• 238000011321 prophylaxis Methods 0.000 claims description 12
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000004450 alkenylene group Chemical group 0.000 claims description 9
• 125000004419 alkynylene group Chemical group 0.000 claims description 9
• JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
• NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 8
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 229960002657 orciprenaline Drugs 0.000 claims description 8
• 229960002052 salbutamol Drugs 0.000 claims description 8
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 7
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 229940044551 receptor antagonist Drugs 0.000 claims description 6
• 239000002464 receptor antagonist Substances 0.000 claims description 6
• 102000003787 Anoctamin-1 Human genes 0.000 claims description 5
• 108090000160 Anoctamin-1 Proteins 0.000 claims description 5
• 239000000443 aerosol Substances 0.000 claims description 5
• 150000001768 cations Chemical class 0.000 claims description 5
• 238000006268 reductive amination reaction Methods 0.000 claims description 5
• XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• ZKLPARSLTMPFCP-OAQYLSRUSA-N 2-[2-[4-[(R)-(4-chlorophenyl)-phenylmethyl]-1-piperazinyl]ethoxy]acetic acid Chemical compound C1CN(CCOCC(=O)O)CCN1[C@@H](C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-OAQYLSRUSA-N 0.000 claims description 4
• MBUVEWMHONZEQD-UHFFFAOYSA-N Azeptin Chemical compound C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 MBUVEWMHONZEQD-UHFFFAOYSA-N 0.000 claims description 4
• KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 claims description 4
• VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 4
• ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims description 4
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 4
• UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 claims description 4
• JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 claims description 4
• VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 claims description 4
• GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims description 4
• YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 claims description 4
• 239000000556 agonist Substances 0.000 claims description 4
• 150000003863 ammonium salts Chemical class 0.000 claims description 4
• 239000003242 anti bacterial agent Substances 0.000 claims description 4
• 229940088710 antibiotic agent Drugs 0.000 claims description 4
• 239000000739 antihistaminic agent Substances 0.000 claims description 4
• 229940125715 antihistaminic agent Drugs 0.000 claims description 4
• GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 claims description 4
• 229960004574 azelastine Drugs 0.000 claims description 4
• 229950000210 beclometasone dipropionate Drugs 0.000 claims description 4
• 229960000585 bitolterol mesylate Drugs 0.000 claims description 4
• HODFCFXCOMKRCG-UHFFFAOYSA-N bitolterol mesylate Chemical compound CS([O-])(=O)=O.C1=CC(C)=CC=C1C(=O)OC1=CC=C(C(O)C[NH2+]C(C)(C)C)C=C1OC(=O)C1=CC=C(C)C=C1 HODFCFXCOMKRCG-UHFFFAOYSA-N 0.000 claims description 4
• 201000009267 bronchiectasis Diseases 0.000 claims description 4
• 229960004436 budesonide Drugs 0.000 claims description 4
• 229960001803 cetirizine Drugs 0.000 claims description 4
• 229960003291 chlorphenamine Drugs 0.000 claims description 4
• SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 claims description 4
• 239000003246 corticosteroid Substances 0.000 claims description 4
• 229960001334 corticosteroids Drugs 0.000 claims description 4
• 229960001271 desloratadine Drugs 0.000 claims description 4
• 108010067396 dornase alfa Proteins 0.000 claims description 4
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 4
• 229960003592 fexofenadine Drugs 0.000 claims description 4
• 229960000676 flunisolide Drugs 0.000 claims description 4
• 229960001469 fluticasone furoate Drugs 0.000 claims description 4
• XTULMSXFIHGYFS-VLSRWLAYSA-N fluticasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(F)[C@@]4(C)C=CC(=O)C=C4[C@@H](F)C[C@H]3[C@@H]2C[C@H]1C)C(=O)SCF)C(=O)C1=CC=CO1 XTULMSXFIHGYFS-VLSRWLAYSA-N 0.000 claims description 4
• 229960000289 fluticasone propionate Drugs 0.000 claims description 4
• WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 claims description 4
• 229960002848 formoterol Drugs 0.000 claims description 4
• BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims description 4
• 229960004078 indacaterol Drugs 0.000 claims description 4
• QZZUEBNBZAPZLX-QFIPXVFZSA-N indacaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 QZZUEBNBZAPZLX-QFIPXVFZSA-N 0.000 claims description 4
• 229960001317 isoprenaline Drugs 0.000 claims description 4
• 229940039009 isoproterenol Drugs 0.000 claims description 4
• 230000000155 isotopic effect Effects 0.000 claims description 4
• 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 4
• 229960001508 levocetirizine Drugs 0.000 claims description 4
• 229960003088 loratadine Drugs 0.000 claims description 4
• JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims description 4
• 229960002744 mometasone furoate Drugs 0.000 claims description 4
• WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 claims description 4
• 229960005127 montelukast Drugs 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 229960005414 pirbuterol Drugs 0.000 claims description 4
• 229960005205 prednisolone Drugs 0.000 claims description 4
• OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 4
• 229960004618 prednisone Drugs 0.000 claims description 4
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 4
• MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 claims description 4
• 230000000241 respiratory effect Effects 0.000 claims description 4
• 229960004017 salmeterol Drugs 0.000 claims description 4
• 229960000195 terbutaline Drugs 0.000 claims description 4
• 229960002117 triamcinolone acetonide Drugs 0.000 claims description 4
• YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 claims description 4
• 229960004764 zafirlukast Drugs 0.000 claims description 4
• 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
• 206010006451 bronchitis Diseases 0.000 claims description 3
• 125000002091 cationic group Chemical group 0.000 claims description 3
• 208000007451 chronic bronchitis Diseases 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
• MJUVRTYWUMPBTR-MRXNPFEDSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-n-[1-[(2r)-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]cyclopropane-1-carboxamide Chemical compound FC=1C=C2N(C[C@@H](O)CO)C(C(C)(CO)C)=CC2=CC=1NC(=O)C1(C=2C=C3OC(F)(F)OC3=CC=2)CC1 MJUVRTYWUMPBTR-MRXNPFEDSA-N 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
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 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
• 229960001340 histamine Drugs 0.000 claims description 2
• 206010021198 ichthyosis Diseases 0.000 claims description 2
• UFSKUSARDNFIRC-UHFFFAOYSA-N lumacaftor Chemical compound N1=C(C=2C=C(C=CC=2)C(O)=O)C(C)=CC=C1NC(=O)C1(C=2C=C3OC(F)(F)OC3=CC=2)CC1 UFSKUSARDNFIRC-UHFFFAOYSA-N 0.000 claims description 2
• 229960000998 lumacaftor Drugs 0.000 claims description 2
• 201000009266 primary ciliary dyskinesia Diseases 0.000 claims description 2
• 230000008439 repair process Effects 0.000 claims description 2
• 239000007921 spray Substances 0.000 claims description 2
• 229950005823 tezacaftor Drugs 0.000 claims description 2
• 238000002560 therapeutic procedure Methods 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 229940124056 Histamine H1 receptor antagonist Drugs 0.000 claims 2
• 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
• 239000000938 histamine H1 antagonist Substances 0.000 claims 2
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• 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
• 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 1
• GHWNFBVNXXWHKP-UHFFFAOYSA-O 3-amino-7-cyano-N-[(1,3-diethyl-5-methoxybenzimidazol-1-ium-2-yl)methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound C([N+]=1C2=CC=C(C=C2N(C=1CNC(=O)C1=NC2=C(NC=C2C#N)N=C1N)CC)OC)C GHWNFBVNXXWHKP-UHFFFAOYSA-O 0.000 claims 1
• PJNCUNIQYCKDJZ-UHFFFAOYSA-O 3-amino-N-[(1,3-diethyl-5-methoxybenzimidazol-1-ium-2-yl)methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound [N+]=1(CC)C2=C(N(C=1CNC(=O)C1=NC3=C(NC=C3)N=C1N)CC)C=C(OC)C=C2 PJNCUNIQYCKDJZ-UHFFFAOYSA-O 0.000 claims 1
• ZFIRRQGRMPREAT-UHFFFAOYSA-O 3-amino-N-[(1,3-diethyl-5-piperidin-4-ylbenzimidazol-1-ium-2-yl)methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound [N+]=1(CC)C2=C(N(C=1CNC(=O)C1=C(N=C3NC=CC3=N1)N)CC)C=C(C1CCNCC1)C=C2 ZFIRRQGRMPREAT-UHFFFAOYSA-O 0.000 claims 1
• GPWMBXZBQSAMSF-UHFFFAOYSA-O 3-amino-N-[(1-benzyl-3-ethyl-5-methoxybenzimidazol-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)OC)CC1=CC=CC=C1 GPWMBXZBQSAMSF-UHFFFAOYSA-O 0.000 claims 1
• ZCJNYEXAGDMZHI-UHFFFAOYSA-O 3-amino-N-[(1-benzyl-3-methylbenzimidazol-3-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)CC1=CC=CC=C1)C=CC=C2)C ZCJNYEXAGDMZHI-UHFFFAOYSA-O 0.000 claims 1
• HHJWGBPUYFUUMB-UHFFFAOYSA-O 3-amino-N-[(1-benzyl-5-chloro-3-ethylbenzimidazol-1-ium-2-yl)methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](Cc2ccccc2)c2ccc(Cl)cc12 HHJWGBPUYFUUMB-UHFFFAOYSA-O 0.000 claims 1
• KLGOCKHUIPKFQR-UHFFFAOYSA-O 3-amino-N-[(1-ethyl-3-methylbenzimidazol-3-ium-2-yl)methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](C)c2ccccc12 KLGOCKHUIPKFQR-UHFFFAOYSA-O 0.000 claims 1
• FXLUWGIMLWZSHW-UHFFFAOYSA-O 3-amino-N-[(3-ethyl-5-fluoro-1-methylbenzimidazol-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(F)C=C2)C FXLUWGIMLWZSHW-UHFFFAOYSA-O 0.000 claims 1
• UBIXDVWBUCUTSB-UHFFFAOYSA-O 3-amino-N-[(3-ethyl-5-methoxy-1-methylbenzimidazol-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(OC)C=C2)C UBIXDVWBUCUTSB-UHFFFAOYSA-O 0.000 claims 1
• 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 1
• QIKDDKCSXHAWRC-UHFFFAOYSA-O 3-amino-N-[(5-chloro-1,3-diethylbenzimidazol-1-ium-2-yl)methyl]-7-methyl-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCn1c(CNC(=O)c2nc3c(C)c[nH]c3nc2N)[n+](CC)c2ccc(Cl)cc12 QIKDDKCSXHAWRC-UHFFFAOYSA-O 0.000 claims 1
• VONCJBOWLJJZBB-UHFFFAOYSA-O 3-amino-N-[(5-chloro-3-ethyl-1-methylbenzimidazol-1-ium-2-yl)methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](C)c2ccc(Cl)cc12 VONCJBOWLJJZBB-UHFFFAOYSA-O 0.000 claims 1
• TXZMMONIBBPVDA-UHFFFAOYSA-O 3-amino-N-[[1,3-diethyl-5-(piperidin-4-ylcarbamoyl)benzimidazol-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)NC1CCNCC1 TXZMMONIBBPVDA-UHFFFAOYSA-O 0.000 claims 1
• 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 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
• AJOZFTMTZVXIOU-UOOXCUFBSA-O 3-amino-N-[[1,3-diethyl-5-[[1-[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]piperidin-4-yl]carbamoyl]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(NC1CCN(CC1)C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)=O)CC AJOZFTMTZVXIOU-UOOXCUFBSA-O 0.000 claims 1
• PITYONBUYUXOOM-UHFFFAOYSA-O 3-amino-N-[[1-(2-amino-2-oxoethyl)-3-ethyl-5-methoxybenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound NC(=O)C[N+]=1C2=C(N(C=1CNC(=O)C1=NC3=C(NC=C3)N=C1N)CC)C=C(OC)C=C2 PITYONBUYUXOOM-UHFFFAOYSA-O 0.000 claims 1
• 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 1
• YSSYJBCXQZDPTO-UHFFFAOYSA-O 3-amino-N-[[1-benzyl-3-ethyl-5-(trifluoromethyl)benzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](Cc2ccccc2)c2ccc(cc12)C(F)(F)F YSSYJBCXQZDPTO-UHFFFAOYSA-O 0.000 claims 1
• IEFMAIBEMZFQBC-UHFFFAOYSA-O 3-amino-N-[[3-ethyl-1-(2-hydroxyethyl)-5-methoxybenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound CCn1c(CNC(=O)c2nc3cc[nH]c3nc2N)[n+](CCO)c2ccc(OC)cc12 IEFMAIBEMZFQBC-UHFFFAOYSA-O 0.000 claims 1
• 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 1
• 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 1
• PTKYINYLDWWHFW-UHFFFAOYSA-O 3-amino-N-[[5-(2-aminoethoxy)-1,3-diethylbenzimidazol-1-ium-2-yl]methyl]-5H-pyrrolo[2,3-b]pyrazine-2-carboxamide Chemical compound [N+]=1(CC)C2=C(N(C=1CNC(=O)C1=NC3=C(N=C1N)NC=C3)CC)C=C(OCCN)C=C2 PTKYINYLDWWHFW-UHFFFAOYSA-O 0.000 claims 1
• NUANEFTVLFRIJA-UHFFFAOYSA-O 3-amino-N-[[5-(3-aminopropoxy)-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)OCCCN)CC NUANEFTVLFRIJA-UHFFFAOYSA-O 0.000 claims 1
• LXRWEJQWQSYGHB-UHFFFAOYSA-O 3-amino-N-[[5-(3-aminopropyl)-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)CCCN)CC LXRWEJQWQSYGHB-UHFFFAOYSA-O 0.000 claims 1
• FQGOGPGHYIAWBT-UHFFFAOYSA-O 3-amino-N-[[5-(4-aminopiperidine-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)N1CCC(N)CC1 FQGOGPGHYIAWBT-UHFFFAOYSA-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
• BGMWMUPICCKRCP-BLXFODJKSA-O 3-amino-N-[[5-[(3S)-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-BLXFODJKSA-O 0.000 claims 1
• LJMSWUPNBYNSQO-UHFFFAOYSA-O 3-amino-N-[[5-[2-(diaminomethylideneamino)ethoxy]-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(OCCN=C(N)N)cc12 LJMSWUPNBYNSQO-UHFFFAOYSA-O 0.000 claims 1
• 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 1
• 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 1
• LYJSIDMCIJCCEU-UHFFFAOYSA-O 3-amino-N-[[5-[3-(diaminomethylideneamino)propyl]-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(CCCN=C(N)N)cc12 LYJSIDMCIJCCEU-UHFFFAOYSA-O 0.000 claims 1
• 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 1
• XKRLSGWYVUQDQR-LTZVJRNQSA-O 3-amino-N-[[5-[3-[bis[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]amino]propyl-methylcarbamoyl]-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(N(C)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)=O)CC XKRLSGWYVUQDQR-LTZVJRNQSA-O 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• XLMFZZXZADBTKZ-UHFFFAOYSA-N CCN1C(C=C(C=C2)C([O-])=O)=C2[N+](CC)=C1CNC(C1=NC(C=CN2)=C2N=C1N)=O Chemical compound CCN1C(C=C(C=C2)C([O-])=O)=C2[N+](CC)=C1CNC(C1=NC(C=CN2)=C2N=C1N)=O XLMFZZXZADBTKZ-UHFFFAOYSA-N 0.000 claims 1
• HPEHSARCIASQIO-UHFFFAOYSA-N CCN1C2=CC(C([O-])=O)=CC=C2[N+](CC)=C1CNC(C1=NC(C(Br)=CN2)=C2N=C1N)=O Chemical compound CCN1C2=CC(C([O-])=O)=CC=C2[N+](CC)=C1CNC(C1=NC(C(Br)=CN2)=C2N=C1N)=O HPEHSARCIASQIO-UHFFFAOYSA-N 0.000 claims 1
• BTTGSQXOYRBGAT-UHFFFAOYSA-N CCN1C2=CC(C([O-])=O)=CC=C2[N+](CC)=C1CNC(C1=NC(C(Cl)=CN2)=C2N=C1N)=O Chemical compound CCN1C2=CC(C([O-])=O)=CC=C2[N+](CC)=C1CNC(C1=NC(C(Cl)=CN2)=C2N=C1N)=O BTTGSQXOYRBGAT-UHFFFAOYSA-N 0.000 claims 1
• RIJVOCZFSKOCSQ-UHFFFAOYSA-O methyl 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)OC RIJVOCZFSKOCSQ-UHFFFAOYSA-O 0.000 claims 1
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• YLALMIZTMNSMLT-UHFFFAOYSA-O tert-butyl 4-[4-[2-[[(3-amino-5H-pyrrolo[2,3-b]pyrazine-2-carbonyl)amino]methyl]-1,3-diethylbenzimidazol-1-ium-5-yl]pyrazol-1-yl]piperidine-1-carboxylate Chemical compound [N+]=1(CC)C2=C(N(C=1CNC(=O)C1=C(N)N=C3NC=CC3=N1)CC)C=C(C1=CN(N=C1)C1CCN(CC1)C(=O)OC(C)(C)C)C=C2 YLALMIZTMNSMLT-UHFFFAOYSA-O 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
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