NO863228L

NO863228L - Fremgangsmaate for fremstilling av farmakodynamisk aktive benzimidazol-derivater.

Fremgangsmaate for fremstilling av farmakodynamisk aktive benzimidazol-derivater.

Info

Publication number: NO863228L
Authority: NO; Norway
Prior art keywords: methyl; methoxy; alkyl; imidazol; solution
Prior art date: 1985-08-12

Application number

NO863228A

Other languages

English (en)

Norwegian (no)

Other versions

NO863228D0 (no

Inventor

Albert Fischli

Anna Krasso

Andre Szente

Original Assignee

Hoffmann La Roche

Priority date

1985-08-12

Filing date

1986-08-11

Publication date

1987-02-13

1986-08-11 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1986-08-11 Publication of NO863228D0 publication Critical patent/NO863228D0/no

1987-02-13 Publication of NO863228L publication Critical patent/NO863228L/no

Links

238000000034 method Methods 0.000 title claims description 26
238000002360 preparation method Methods 0.000 title claims description 12
230000003285 pharmacodynamic effect Effects 0.000 title description 4
229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
150000001556 benzimidazoles Chemical class 0.000 title description 2
-1 (C2 -C7 )-alkanoyl Chemical group 0.000 claims description 266
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 129
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 67
150000001875 compounds Chemical class 0.000 claims description 56
125000004119 disulfanediyl group Chemical group *SS* 0.000 claims description 50
239000001257 hydrogen Substances 0.000 claims description 44
229910052739 hydrogen Inorganic materials 0.000 claims description 44
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
150000003839 salts Chemical class 0.000 claims description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
229910052740 iodine Inorganic materials 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 10
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 10
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 8
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 8
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 7
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 6
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
ILROLYQPRYHHFG-UHFFFAOYSA-N 1-$l^{1}-oxidanylprop-2-en-1-one Chemical group [O]C(=O)C=C ILROLYQPRYHHFG-UHFFFAOYSA-N 0.000 claims description 5
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 5
XOPFPFXWJMHARA-UHFFFAOYSA-N 2-pyridin-1-ium-1-yl-1h-benzimidazole Chemical class C1=CC=CC=[N+]1C1=NC2=CC=CC=C2N1 XOPFPFXWJMHARA-UHFFFAOYSA-N 0.000 claims description 5
108010038807 Oligopeptides Proteins 0.000 claims description 5
102000015636 Oligopeptides Human genes 0.000 claims description 5
208000025865 Ulcer Diseases 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 5
235000018417 cysteine Nutrition 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
210000001198 duodenum Anatomy 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 5
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
231100000397 ulcer Toxicity 0.000 claims description 5
LNQOPXFJCSWYIC-UHFFFAOYSA-M 2-[4-methoxy-3-methyl-2-[(propyldisulfanyl)methyl]pyridin-1-ium-1-yl]-6-(trifluoromethyl)-1h-benzimidazole;chloride Chemical compound [Cl-].CCCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC=C(C(F)(F)F)C=C2N1 LNQOPXFJCSWYIC-UHFFFAOYSA-M 0.000 claims description 4
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 4
RZUKEWKLVDAGJK-UHFFFAOYSA-M 2-[2-[(2-hydroxyethyldisulfanyl)methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].OCCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 RZUKEWKLVDAGJK-UHFFFAOYSA-M 0.000 claims description 3
CFBRIIHONDCBRS-UHFFFAOYSA-M 2-[2-[(ethyldisulfanyl)methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 CFBRIIHONDCBRS-UHFFFAOYSA-M 0.000 claims description 3
HMKPDQUZPMPAJJ-UHFFFAOYSA-M 2-[2-[[(2-chlorophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-6-(trifluoromethyl)-1h-benzimidazole;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC(=CC=C3N=2)C(F)(F)F)C=1CSSC1=CC=CC=C1Cl HMKPDQUZPMPAJJ-UHFFFAOYSA-M 0.000 claims description 3
BIIWSJODXLMNCZ-UHFFFAOYSA-M 2-[2-[[(3-chlorophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=CC(Cl)=C1 BIIWSJODXLMNCZ-UHFFFAOYSA-M 0.000 claims description 3
OHDKYWIUKSEZEE-UHFFFAOYSA-M 2-[4-methoxy-3-methyl-2-[(propyldisulfanyl)methyl]pyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CCCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 OHDKYWIUKSEZEE-UHFFFAOYSA-M 0.000 claims description 3
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
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 3
229940079593 drug Drugs 0.000 claims description 3
230000008030 elimination Effects 0.000 claims description 3
238000003379 elimination reaction Methods 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
125000005646 oximino group Chemical group 0.000 claims description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
125000004542 purin-6-yl group Chemical group N1=CN=C2N=CNC2=C1* 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
CEMOLVHEGJKRQG-UHFFFAOYSA-M 2-[2-[(cyclopentyldisulfanyl)methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1CCCC1 CEMOLVHEGJKRQG-UHFFFAOYSA-M 0.000 claims description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
XOVXCCPPIISFAJ-UHFFFAOYSA-M diethyl 2-[[4-methoxy-3-methyl-1-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]pyridin-1-ium-2-yl]methyldisulfanyl]butanedioate;chloride Chemical compound [Cl-].CCOC(=O)CC(C(=O)OCC)SSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC=C(C(F)(F)F)C=C2N1 XOVXCCPPIISFAJ-UHFFFAOYSA-M 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
DNMMXBMPGHZLOS-UHFFFAOYSA-N 2-[2-[(ethyldisulfanyl)methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound CCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC=C(C(F)(F)F)C=C2N1 DNMMXBMPGHZLOS-UHFFFAOYSA-N 0.000 claims 1
HDJVOROQYVGKQY-UHFFFAOYSA-M 2-[2-[(hexyldisulfanyl)methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-6-(trifluoromethyl)-1h-benzimidazole;chloride Chemical compound [Cl-].CCCCCCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC=C(C(F)(F)F)C=C2N1 HDJVOROQYVGKQY-UHFFFAOYSA-M 0.000 claims 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 365
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 360
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 336
239000000243 solution Substances 0.000 description 325
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 290
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 257
238000002844 melting Methods 0.000 description 213
230000008018 melting Effects 0.000 description 213
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 208
238000000354 decomposition reaction Methods 0.000 description 135
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 130
239000011541 reaction mixture Substances 0.000 description 122
238000003756 stirring Methods 0.000 description 117
239000000203 mixture Substances 0.000 description 91
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 88
229960000583 acetic acid Drugs 0.000 description 88
YBCJDBBYBFMVEG-UHFFFAOYSA-N Ro 18-5364 Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)=C1C YBCJDBBYBFMVEG-UHFFFAOYSA-N 0.000 description 74
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 65
238000002425 crystallisation Methods 0.000 description 63
230000008025 crystallization Effects 0.000 description 63
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 54
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 52
239000000047 product Substances 0.000 description 49
239000000052 vinegar Substances 0.000 description 46
235000021419 vinegar Nutrition 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
239000002244 precipitate Substances 0.000 description 43
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
238000001816 cooling Methods 0.000 description 39
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 37
239000002904 solvent Substances 0.000 description 36
239000012265 solid product Substances 0.000 description 35
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
235000019439 ethyl acetate Nutrition 0.000 description 30
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
229910052786 argon Inorganic materials 0.000 description 27
239000000741 silica gel Substances 0.000 description 25
229910002027 silica gel Inorganic materials 0.000 description 25
229910000029 sodium carbonate Inorganic materials 0.000 description 25
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 25
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 24
229910000041 hydrogen chloride Inorganic materials 0.000 description 23
239000003208 petroleum Substances 0.000 description 23
229910052938 sodium sulfate Inorganic materials 0.000 description 23
235000011152 sodium sulphate Nutrition 0.000 description 22
238000010992 reflux Methods 0.000 description 21
239000007795 chemical reaction product Substances 0.000 description 20
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
239000012074 organic phase Substances 0.000 description 19
PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 18
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 18
OWWKQFJLNQHYQS-UHFFFAOYSA-N 2-[(4-methoxy-3-methylpyridin-2-yl)methylsulfinyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC(=CC=C3N=2)C(F)(F)F)=C1C OWWKQFJLNQHYQS-UHFFFAOYSA-N 0.000 description 15
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
235000011121 sodium hydroxide Nutrition 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 13
NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
229910001873 dinitrogen Inorganic materials 0.000 description 11
238000003818 flash chromatography Methods 0.000 description 11
238000001953 recrystallisation Methods 0.000 description 11
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 11
HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 description 10
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HENJILSUFJLLPG-UHFFFAOYSA-M 2-[2-[(cyclohexyldisulfanyl)methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1CCCCC1 HENJILSUFJLLPG-UHFFFAOYSA-M 0.000 description 1
CPAJEUZNWNWNKC-UHFFFAOYSA-M 2-[2-[(dodecyldisulfanyl)methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CCCCCCCCCCCCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 CPAJEUZNWNWNKC-UHFFFAOYSA-M 0.000 description 1
WNUKSFBVLYVCQE-UHFFFAOYSA-M 2-[2-[(dodecyldisulfanyl)methyl]pyridin-1-ium-1-yl]-1h-benzimidazole;chloride Chemical compound [Cl-].CCCCCCCCCCCCSSCC1=CC=CC=[N+]1C1=NC2=CC=CC=C2N1 WNUKSFBVLYVCQE-UHFFFAOYSA-M 0.000 description 1
IOMBSUKAPMTURQ-UHFFFAOYSA-M 2-[2-[(ethyldisulfanyl)methyl]-3-methylpyridin-1-ium-1-yl]-6-(trifluoromethyl)-1H-benzimidazole chloride Chemical compound [Cl-].CCSSCC1=C(C)C=CC=[N+]1C1=NC2=CC=C(C(F)(F)F)C=C2N1 IOMBSUKAPMTURQ-UHFFFAOYSA-M 0.000 description 1
WAQUATHLXQMROP-UHFFFAOYSA-M 2-[2-[(ethyldisulfanyl)methyl]-4-methoxy-3,5-dimethylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CCSSCC1=C(C)C(OC)=C(C)C=[N+]1C1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 WAQUATHLXQMROP-UHFFFAOYSA-M 0.000 description 1
XYTXELCNSWEMIG-UHFFFAOYSA-M 2-[2-[(ethyldisulfanyl)methyl]-4-methoxy-3,5-dimethylpyridin-1-ium-1-yl]-6-methoxy-1h-benzimidazole;chloride Chemical compound [Cl-].CCSSCC1=C(C)C(OC)=C(C)C=[N+]1C1=NC2=CC=C(OC)C=C2N1 XYTXELCNSWEMIG-UHFFFAOYSA-M 0.000 description 1
LYHPOQUOFXQDEY-UHFFFAOYSA-M 2-[2-[(ethyldisulfanyl)methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5h-[1,3]dioxolo[4,5-f]benzimidazole;chloride;hydrochloride Chemical compound Cl.[Cl-].CCSSCC1=C(C)C(OC)=CC=[N+]1C1OC2=CC(NC=N3)=C3C=C2O1 LYHPOQUOFXQDEY-UHFFFAOYSA-M 0.000 description 1
STXIVTPMKRRBSN-UHFFFAOYSA-M 2-[2-[(ethyldisulfanyl)methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-6-(trifluoromethyl)-1h-benzimidazole;chloride Chemical compound [Cl-].CCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC=C(C(F)(F)F)C=C2N1 STXIVTPMKRRBSN-UHFFFAOYSA-M 0.000 description 1
ODLKEJABUHFJLZ-UHFFFAOYSA-M 2-[2-[(ethyldisulfanyl)methyl]pyridin-1-ium-1-yl]-1h-benzimidazole;chloride Chemical compound [Cl-].CCSSCC1=CC=CC=[N+]1C1=NC2=CC=CC=C2N1 ODLKEJABUHFJLZ-UHFFFAOYSA-M 0.000 description 1
DIASRFRWEPBJNO-UHFFFAOYSA-M 2-[2-[(heptyldisulfanyl)methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CCCCCCCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 DIASRFRWEPBJNO-UHFFFAOYSA-M 0.000 description 1
ZHOPBPPRLXXHOL-UHFFFAOYSA-M 2-[2-[(hexyldisulfanyl)methyl]-3-methylpyridin-1-ium-1-yl]-6-(trifluoromethyl)-1h-benzimidazole;chloride Chemical compound [Cl-].CCCCCCSSCC1=C(C)C=CC=[N+]1C1=NC2=CC=C(C(F)(F)F)C=C2N1 ZHOPBPPRLXXHOL-UHFFFAOYSA-M 0.000 description 1
WOEYGZIAWPSINT-UHFFFAOYSA-M 2-[2-[(hexyldisulfanyl)methyl]-4-methoxy-3,5-dimethylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CCCCCCSSCC1=C(C)C(OC)=C(C)C=[N+]1C1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 WOEYGZIAWPSINT-UHFFFAOYSA-M 0.000 description 1
MPIIRBUVIHEZLR-UHFFFAOYSA-M 2-[2-[(hexyldisulfanyl)methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-6-methoxy-1h-benzimidazole;chloride Chemical compound [Cl-].CCCCCCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC=C(OC)C=C2N1 MPIIRBUVIHEZLR-UHFFFAOYSA-M 0.000 description 1
SRXSQCFSFWYDRG-UHFFFAOYSA-M 2-[2-[(hexyldisulfanyl)methyl]pyridin-1-ium-1-yl]-1h-benzimidazole;chloride Chemical compound [Cl-].CCCCCCSSCC1=CC=CC=[N+]1C1=NC2=CC=CC=C2N1 SRXSQCFSFWYDRG-UHFFFAOYSA-M 0.000 description 1
LJNISKQPYCROJQ-UHFFFAOYSA-M 2-[2-[(propyldisulfanyl)methyl]pyridin-1-ium-1-yl]-1h-benzimidazole;chloride Chemical compound [Cl-].CCCSSCC1=CC=CC=[N+]1C1=NC2=CC=CC=C2N1 LJNISKQPYCROJQ-UHFFFAOYSA-M 0.000 description 1
AFWRUZIUIQBRCC-UHFFFAOYSA-M 2-[2-[[(2,4-dichlorophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=C(Cl)C=C1Cl AFWRUZIUIQBRCC-UHFFFAOYSA-M 0.000 description 1
CIPMFPHCANZKCN-UHFFFAOYSA-M 2-[2-[[(2,6-dichlorophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=C(Cl)C=CC=C1Cl CIPMFPHCANZKCN-UHFFFAOYSA-M 0.000 description 1
UUVHAOJBYHSRMA-UHFFFAOYSA-M 2-[2-[[(2-aminophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride;dihydrochloride Chemical compound Cl.Cl.[Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=CC=C1N UUVHAOJBYHSRMA-UHFFFAOYSA-M 0.000 description 1
PRUJOSCNUBZJAR-UHFFFAOYSA-M 2-[2-[[(2-bromophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=CC=C1Br PRUJOSCNUBZJAR-UHFFFAOYSA-M 0.000 description 1
UFBOCMWUZLTFDY-UHFFFAOYSA-M 2-[2-[[(2-chlorophenyl)disulfanyl]methyl]-3,5-dimethylpyridin-1-ium-1-yl]-6-(trifluoromethyl)-1h-benzimidazole;chloride Chemical compound [Cl-].N=1C2=CC=C(C(F)(F)F)C=C2NC=1[N+]1=CC(C)=CC(C)=C1CSSC1=CC=CC=C1Cl UFBOCMWUZLTFDY-UHFFFAOYSA-M 0.000 description 1
GVLQVCMLJVUCRU-UHFFFAOYSA-M 2-[2-[[(2-chlorophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-6-methoxy-1h-benzimidazole;chloride Chemical compound [Cl-].N1C2=CC(OC)=CC=C2N=C1[N+]1=CC=C(OC)C(C)=C1CSSC1=CC=CC=C1Cl GVLQVCMLJVUCRU-UHFFFAOYSA-M 0.000 description 1
KMDXRJWDMVNHET-UHFFFAOYSA-M 2-[2-[[(3,4-dichlorophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=C(Cl)C(Cl)=C1 KMDXRJWDMVNHET-UHFFFAOYSA-M 0.000 description 1
NWGIABQFYJQRPE-UHFFFAOYSA-M 2-[2-[[(3,4-dichlorophenyl)methyldisulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSCC1=CC=C(Cl)C(Cl)=C1 NWGIABQFYJQRPE-UHFFFAOYSA-M 0.000 description 1
RDOLQGZAJYYSKA-UHFFFAOYSA-M 2-[2-[[(3-aminophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride;hydrochloride Chemical compound Cl.[Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=CC(N)=C1 RDOLQGZAJYYSKA-UHFFFAOYSA-M 0.000 description 1
QZUUFINRTLLKRH-UHFFFAOYSA-M 2-[2-[[(3-chlorophenyl)disulfanyl]methyl]-4-methoxy-3,5-dimethylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=C(C)C=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=CC(Cl)=C1 QZUUFINRTLLKRH-UHFFFAOYSA-M 0.000 description 1
KUPSFDIZMFNSKQ-UHFFFAOYSA-M 2-[2-[[(3-chlorophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-6-(trifluoromethyl)-1h-benzimidazole;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC(=CC=C3N=2)C(F)(F)F)C=1CSSC1=CC=CC(Cl)=C1 KUPSFDIZMFNSKQ-UHFFFAOYSA-M 0.000 description 1
LBDYIMXVFUHFSB-UHFFFAOYSA-M 2-[2-[[(3-fluorophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=CC(F)=C1 LBDYIMXVFUHFSB-UHFFFAOYSA-M 0.000 description 1
MTHFCOXITRELFD-UHFFFAOYSA-M 2-[2-[[(4,6-dimethylpyrimidin-2-yl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=NC(C)=CC(C)=N1 MTHFCOXITRELFD-UHFFFAOYSA-M 0.000 description 1
JDTRFGXUGRDJQP-UHFFFAOYSA-M 2-[2-[[(4-chlorophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=C(Cl)C=C1 JDTRFGXUGRDJQP-UHFFFAOYSA-M 0.000 description 1
VTZQGBSEARWUEE-UHFFFAOYSA-M 2-[2-[[(4-chlorophenyl)methyldisulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSCC1=CC=C(Cl)C=C1 VTZQGBSEARWUEE-UHFFFAOYSA-M 0.000 description 1
VAECVPHQYFAPHI-UHFFFAOYSA-M 2-[2-[[(4-fluorophenyl)disulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=C(F)C=C1 VAECVPHQYFAPHI-UHFFFAOYSA-M 0.000 description 1
NHEUGGCFVYNGGS-UHFFFAOYSA-M 2-[2-[[(4-methylphenyl)disulfanyl]methyl]pyridin-1-ium-1-yl]-1h-benzimidazole;chloride Chemical compound [Cl-].C1=CC(C)=CC=C1SSCC1=CC=CC=[N+]1C1=NC2=CC=CC=C2N1 NHEUGGCFVYNGGS-UHFFFAOYSA-M 0.000 description 1
DJLOKPBVQLCPGI-UHFFFAOYSA-N 2-[2-[[2-(dimethylamino)ethyldisulfanyl]methyl]-4-methoxy-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one Chemical class CN(C)CCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 DJLOKPBVQLCPGI-UHFFFAOYSA-N 0.000 description 1
LBDPUSMLIQNGHY-UHFFFAOYSA-M 2-[3,5-dimethyl-2-[(propyldisulfanyl)methyl]pyridin-1-ium-1-yl]-6-(trifluoromethyl)-1h-benzimidazole;chloride Chemical compound [Cl-].CCCSSCC1=C(C)C=C(C)C=[N+]1C1=NC2=CC=C(C(F)(F)F)C=C2N1 LBDPUSMLIQNGHY-UHFFFAOYSA-M 0.000 description 1
MTSUWGFRWAXBPD-UHFFFAOYSA-M 2-[3-methyl-2-[(propyldisulfanyl)methyl]pyridin-1-ium-1-yl]-6-(trifluoromethyl)-1h-benzimidazole;chloride Chemical compound [Cl-].CCCSSCC1=C(C)C=CC=[N+]1C1=NC2=CC=C(C(F)(F)F)C=C2N1 MTSUWGFRWAXBPD-UHFFFAOYSA-M 0.000 description 1
VWVNTMOFHITIRX-UHFFFAOYSA-M 2-[4-methoxy-2-[[(4-methoxyphenyl)methyldisulfanyl]methyl]-3-methylpyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride;hydrochloride Chemical compound Cl.[Cl-].C1=CC(OC)=CC=C1CSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 VWVNTMOFHITIRX-UHFFFAOYSA-M 0.000 description 1
GSRGTPAKZYOAQL-UHFFFAOYSA-M 2-[4-methoxy-3,5-dimethyl-2-[(propyldisulfanyl)methyl]pyridin-1-ium-1-yl]-1h-benzimidazole;chloride Chemical compound [Cl-].CCCSSCC1=C(C)C(OC)=C(C)C=[N+]1C1=NC2=CC=CC=C2N1 GSRGTPAKZYOAQL-UHFFFAOYSA-M 0.000 description 1
RHTSNHVHBPGNSK-UHFFFAOYSA-M 2-[4-methoxy-3-methyl-2-[(1h-1,2,4-triazol-5-yldisulfanyl)methyl]pyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC=1N=CNN=1 RHTSNHVHBPGNSK-UHFFFAOYSA-M 0.000 description 1
NSXBSVJHXGRJCI-UHFFFAOYSA-M 2-[4-methoxy-3-methyl-2-[(2-phenylethyldisulfanyl)methyl]pyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSCCC1=CC=CC=C1 NSXBSVJHXGRJCI-UHFFFAOYSA-M 0.000 description 1
JCRYBPNHMFLJDL-UHFFFAOYSA-M 2-[4-methoxy-3-methyl-2-[(7h-purin-6-yldisulfanyl)methyl]pyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride;hydrochloride Chemical compound Cl.[Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=NC=NC2=C1NC=N2 JCRYBPNHMFLJDL-UHFFFAOYSA-M 0.000 description 1
KUVRGTOROHCVMT-UHFFFAOYSA-M 2-[4-methoxy-3-methyl-2-[(octadecyldisulfanyl)methyl]pyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 KUVRGTOROHCVMT-UHFFFAOYSA-M 0.000 description 1
QZYDJPAJWRRQHP-UHFFFAOYSA-M 2-[4-methoxy-3-methyl-2-[(phenyldisulfanyl)methyl]pyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=CC=C1 QZYDJPAJWRRQHP-UHFFFAOYSA-M 0.000 description 1
WLNOYHNLVIAXNB-UHFFFAOYSA-M 2-[4-methoxy-3-methyl-2-[[(2-methylphenyl)disulfanyl]methyl]pyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=CC=C1C WLNOYHNLVIAXNB-UHFFFAOYSA-M 0.000 description 1
MQJHOCCRYURKKB-UHFFFAOYSA-M 2-[4-methoxy-3-methyl-2-[[(3-nitrophenyl)methyldisulfanyl]methyl]pyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSCC1=CC=CC([N+]([O-])=O)=C1 MQJHOCCRYURKKB-UHFFFAOYSA-M 0.000 description 1
KIOFFXHAGVBXOQ-UHFFFAOYSA-M 2-[4-methoxy-3-methyl-2-[[(4-methylphenyl)disulfanyl]methyl]pyridin-1-ium-1-yl]-6-(trifluoromethyl)-1h-benzimidazole;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC(=CC=C3N=2)C(F)(F)F)C=1CSSC1=CC=C(C)C=C1 KIOFFXHAGVBXOQ-UHFFFAOYSA-M 0.000 description 1
MKPNWWVFJJQOOF-UHFFFAOYSA-M 2-[4-methoxy-3-methyl-2-[[(4-nitrophenyl)disulfanyl]methyl]pyridin-1-ium-1-yl]-5,5,7,7-tetramethyl-3h-cyclopenta[f]benzimidazol-6-one;chloride Chemical compound [Cl-].CC=1C(OC)=CC=[N+](C=2NC3=CC4=C(C(C(=O)C4(C)C)(C)C)C=C3N=2)C=1CSSC1=CC=C([N+]([O-])=O)C=C1 MKPNWWVFJJQOOF-UHFFFAOYSA-M 0.000 description 1
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