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

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 (The priority date 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 date listed.)

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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IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
KNAHARQHSZJURB-UHFFFAOYSA-N Propylthiouracile Chemical compound CCCC1=CC(=O)NC(=S)N1 KNAHARQHSZJURB-UHFFFAOYSA-N 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical compound CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
CQIQWIMXCPTQPJ-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]methanethiol Chemical compound FC(F)(F)C1=CC=CC(CS)=C1 CQIQWIMXCPTQPJ-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000000556 agonist Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000005038 alkynylalkyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000000767 anti-ulcer Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
230000003139 buffering effect Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
XEKAUTDWPYQNFU-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl XEKAUTDWPYQNFU-UHFFFAOYSA-N 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 1
238000011161 development Methods 0.000 description 1
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
FGRVOLIFQGXPCT-UHFFFAOYSA-L dipotassium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [K+].[K+].[O-]S([O-])(=O)=S FGRVOLIFQGXPCT-UHFFFAOYSA-L 0.000 description 1
230000006806 disease prevention Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
208000000718 duodenal ulcer Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000010931 ester hydrolysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
YVKSGVDJQXLXDV-BYPYZUCNSA-N ethyl (2r)-2-amino-3-sulfanylpropanoate Chemical compound CCOC(=O)[C@@H](N)CS YVKSGVDJQXLXDV-BYPYZUCNSA-N 0.000 description 1
KQDKYFKCIMDBGE-UHFFFAOYSA-M ethyl 2-[[4-methoxy-3-methyl-1-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]pyridin-1-ium-2-yl]methyldisulfanyl]acetate;chloride Chemical compound [Cl-].CCOC(=O)CSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC=C(C(F)(F)F)C=C2N1 KQDKYFKCIMDBGE-UHFFFAOYSA-M 0.000 description 1
XFZVXOBETXPUBN-UHFFFAOYSA-N ethyl 4-tert-butyl-2,3-dimethyl-4h-pyridine-1-carboxylate Chemical compound CCOC(=O)N1C=CC(C(C)(C)C)C(C)=C1C XFZVXOBETXPUBN-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000020251 goat milk Nutrition 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000008011 inorganic excipient Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
239000000463 material Substances 0.000 description 1
NRVFDGZJTPCULU-UHFFFAOYSA-N meda Chemical compound Cl.CN(C)CCS NRVFDGZJTPCULU-UHFFFAOYSA-N 0.000 description 1
229960001428 mercaptopurine Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
KCJYHWZJHJEMNA-UHFFFAOYSA-M methyl 2-[[4-methoxy-3-methyl-1-(5,5,7,7-tetramethyl-6-oxo-3h-cyclopenta[f]benzimidazol-2-yl)pyridin-1-ium-2-yl]methyldisulfanyl]acetate;chloride Chemical compound [Cl-].COC(=O)CSSCC1=C(C)C(OC)=CC=[N+]1C1=NC2=CC(C(C(=O)C3(C)C)(C)C)=C3C=C2N1 KCJYHWZJHJEMNA-UHFFFAOYSA-M 0.000 description 1
MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
AYEQJLOHMLYKAV-UHFFFAOYSA-N n-(4-sulfanylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S)C=C1 AYEQJLOHMLYKAV-UHFFFAOYSA-N 0.000 description 1
125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229960000381 omeprazole Drugs 0.000 description 1
239000008012 organic excipient Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
VVNCNSJFMMFHPL-UHFFFAOYSA-N penicillamine Chemical compound CC(C)(S)C(N)C(O)=O VVNCNSJFMMFHPL-UHFFFAOYSA-N 0.000 description 1
229960001639 penicillamine Drugs 0.000 description 1
210000004303 peritoneum Anatomy 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
238000011160 research Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000028327 secretion Effects 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229950011585 timoprazole Drugs 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/36—Sulfur atom
- C07D473/38—Sulfur atom attached in position 6
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO863228A 1985-08-12 1986-08-11 Fremgangsmaate for fremstilling av farmakodynamisk aktive benzimidazol-derivater. NO863228L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH345585		1985-08-12
CH235086		1986-06-10

Publications (2)

Publication Number	Publication Date
NO863228D0 NO863228D0 (no)	1986-08-11
NO863228L true NO863228L (no)	1987-02-13

Family

ID=25690225

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO863228A NO863228L (no)	1985-08-12	1986-08-11	Fremgangsmaate for fremstilling av farmakodynamisk aktive benzimidazol-derivater.

Country Status (10)

Country	Link
US (1)	US4766133A (fi)
EP (1)	EP0214479A3 (fi)
AU (1)	AU6094386A (fi)
DK (1)	DK337086A (fi)
FI (1)	FI863242A (fi)
HU (1)	HUT41766A (fi)
IL (1)	IL79642A0 (fi)
MC (1)	MC1771A1 (fi)
NO (1)	NO863228L (fi)
PT (1)	PT83188A (fi)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0304624A3 (de) *	1987-07-29	1989-03-22	F. Hoffmann-La Roche Ag	Benzimidazol-2-yl-pyridiniumverbindungen
EP0374261A1 (en) *	1988-05-12	1990-06-27	Eisai Co., Ltd.	Pyridinium salt and pharmacological composition containing the same
US4859679A (en) *	1988-07-19	1989-08-22	Pfizer Inc.	Antiulcer (alkyldithio) quinoline derivatives
AU8946291A (en) *	1990-11-29	1992-06-25	Byk Gulden Lomberg Chemische Fabrik Gmbh	New and known disulphides and their use
WO1993016693A1 (de) *	1992-02-25	1993-09-02	Byk Gulden Lomberg Chemische Fabrik Gmbh	Neue und bekannte disulfide und ihre verwendung gegen helicobacter-bakterien
US6323201B1 (en)	1994-12-29	2001-11-27	The Regents Of The University Of California	Compounds for inhibition of ceramide-mediated signal transduction
US5894597A (en) *	1996-09-24	1999-04-13	Motorola, Inc.	Communication device for different sized cards
DE19745692A1 (de) *	1997-07-24	1999-01-28	Bayer Ag	Verfahren zur Herstellung von 2-Chlor-benzimidazol-Derivaten
US6344330B1 (en) *	1998-03-27	2002-02-05	The Regents Of The University Of California	Pharmacophore recombination for the identification of small molecule drug lead compounds
US6930101B1 (en)	1999-05-17	2005-08-16	The Regents Of The University Of California	Thiazolopyrimidines useful as TNFα inhibitors
WO2006049304A1 (ja) *	2004-11-02	2006-05-11	Banyu Pharmaceutical Co., Ltd	アリールオキシ置換ベンズイミダゾール誘導体
AU2006315090B2 (en) *	2005-11-17	2011-12-15	Jon Pty Limited	Pharmacologically active compounds containing sulfur
US20200247846A1 (en) *	2017-08-14	2020-08-06	The Regents Of The University Of Colorado, A Body Corporate	Inhibition of oxidative stress, glycation, and protein crosslinking

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB993302A (en) *	1963-03-13	1965-05-26	Carter Prod Inc	Nitrogen-containing heterocyclic disulfides
SE416649B (sv) *	1974-05-16	1981-01-26	Haessle Ab	Forfarande for framstellning av foreningar som paverkar magsyrasekretionen
IN148930B (fi) *	1977-09-19	1981-07-25	Hoffmann La Roche
CH644116A5 (de) *	1980-08-21	1984-07-13	Hoffmann La Roche	Imidazolderivate.
US4302464A (en) *	1980-10-16	1981-11-24	Pfizer Inc.	Imidazolylpyridine therapeutic agents
US4472409A (en) *	1981-11-05	1984-09-18	Byk Gulden Lomberg Chemische Fabrik Gesellschaft Mit Beschrankter Haftung	2-Pyridylmethyl thio(sulfinyl)benzimidazoles with gastric acid secretion inhibiting effects
SE8300736D0 (sv) *	1983-02-11	1983-02-11	Haessle Ab	Novel pharmacologically active compounds
ZW4585A1 (en) *	1984-04-19	1985-11-20	Hoffmann La Roche	Imidazole derivatives
SE8405588D0 (sv) *	1984-11-08	1984-11-08	Haessle Ab	New compounds

1986
- 1986-07-15 DK DK337086A patent/DK337086A/da not_active Application Discontinuation
- 1986-08-06 IL IL79642A patent/IL79642A0/xx unknown
- 1986-08-06 US US06/893,856 patent/US4766133A/en not_active Expired - Fee Related
- 1986-08-06 AU AU60943/86A patent/AU6094386A/en not_active Abandoned
- 1986-08-08 MC MC861845A patent/MC1771A1/xx unknown
- 1986-08-08 EP EP86110990A patent/EP0214479A3/de not_active Withdrawn
- 1986-08-08 FI FI863242A patent/FI863242A/fi not_active Application Discontinuation
- 1986-08-08 HU HU863450A patent/HUT41766A/hu unknown
- 1986-08-11 NO NO863228A patent/NO863228L/no unknown
- 1986-08-12 PT PT83188A patent/PT83188A/pt unknown

Also Published As

Publication number	Publication date
EP0214479A3 (de)	1987-08-05
US4766133A (en)	1988-08-23
FI863242A (fi)	1987-02-13
FI863242A0 (fi)	1986-08-08
IL79642A0 (en)	1986-11-30
EP0214479A2 (de)	1987-03-18
NO863228D0 (no)	1986-08-11
DK337086D0 (da)	1986-07-15
DK337086A (da)	1987-02-13
HUT41766A (en)	1987-05-28
AU6094386A (en)	1987-02-19
MC1771A1 (fr)	1987-07-17
PT83188A (en)	1986-09-01

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US5527819A (en)	1996-06-18	Inhibitors of HIV reverse transcriptase
NO120426B (fi)	1970-10-19
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JP2000500745A (ja)	2000-01-25	蛋白質イソプレニルトランスフェラーゼの阻害剤
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JPH0971586A (ja)	1997-03-18	新規な二環性縮合イミダゾール誘導体
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CZ280776B6 (cs)	1996-04-17	Derivát tripeptidu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
JPH0417957B2 (fi)	1992-03-26
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JPH0327363A (ja)	1991-02-05	チオウラシル誘導体
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KR920008168B1 (ko)	1992-09-24	피리미도이소퀴놀린 유도체의 제조방법