NL8003627A - Benzimidazoolderivaten alsmede farmaceutische preparaten en werkwijze voor het bereiden daarvan. - Google Patents
Benzimidazoolderivaten alsmede farmaceutische preparaten en werkwijze voor het bereiden daarvan. Download PDFInfo
- Publication number
- NL8003627A NL8003627A NL8003627A NL8003627A NL8003627A NL 8003627 A NL8003627 A NL 8003627A NL 8003627 A NL8003627 A NL 8003627A NL 8003627 A NL8003627 A NL 8003627A NL 8003627 A NL8003627 A NL 8003627A
- Authority
- NL
- Netherlands
- Prior art keywords
- benzimidazole
- carboxylic acid
- methyl ester
- acid
- tan
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 78
- 150000001556 benzimidazoles Chemical class 0.000 title claims description 18
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 4
- 150000004702 methyl esters Chemical class 0.000 claims description 144
- 150000001875 compounds Chemical class 0.000 claims description 113
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 93
- 150000003839 salts Chemical class 0.000 claims description 75
- COYPLDIXZODDDL-UHFFFAOYSA-N 3h-benzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=CNC2=C1 COYPLDIXZODDDL-UHFFFAOYSA-N 0.000 claims description 54
- -1 2,3-dihydroxyprop-1-yl Chemical group 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 18
- SWSLUNUYJRKPMS-UHFFFAOYSA-N 2-pentadecyl-3h-benzimidazole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2NC(CCCCCCCCCCCCCCC)=NC2=C1 SWSLUNUYJRKPMS-UHFFFAOYSA-N 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 3
- KGMCJQLLJVFPSK-UHFFFAOYSA-N 2-(3h-benzimidazol-5-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2N=CNC2=C1 KGMCJQLLJVFPSK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- SBQDVBVVATWUAF-UHFFFAOYSA-N 2-tridecan-7-yl-3H-benzimidazole-5-carboxylic acid Chemical compound CCCCCCC(CCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O SBQDVBVVATWUAF-UHFFFAOYSA-N 0.000 claims description 2
- DQNUXNFKJKPDNQ-UHFFFAOYSA-N 2-tridecyl-1H-benzimidazole-4-carboxylic acid Chemical compound C(CCCCCCCCCCCC)C=1NC2=C(N=1)C=CC=C2C(=O)O DQNUXNFKJKPDNQ-UHFFFAOYSA-N 0.000 claims description 2
- 206010002329 Aneurysm Diseases 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000000668 Chronic Pancreatitis Diseases 0.000 claims description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 206010033649 Pancreatitis chronic Diseases 0.000 claims description 2
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 2
- 206010053648 Vascular occlusion Diseases 0.000 claims description 2
- 206010048215 Xanthomatosis Diseases 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 210000004720 cerebrum Anatomy 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000026278 immune system disease Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 208000021331 vascular occlusion disease Diseases 0.000 claims description 2
- OPGUZRRLMQSMAQ-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1-phenylbenzimidazole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(C=N2)C=3C=CC=CC=3)C2=C1 OPGUZRRLMQSMAQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- VVQNAFBGAWCMLU-UHFFFAOYSA-N 1h-benzimidazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1N=CN2 VVQNAFBGAWCMLU-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 230000001125 hyperlipoproteinemic effect Effects 0.000 claims 1
- 239000007943 implant Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 206
- 239000007787 solid Substances 0.000 description 185
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 164
- 239000000203 mixture Substances 0.000 description 146
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 141
- 239000000243 solution Substances 0.000 description 140
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 128
- 239000005711 Benzoic acid Substances 0.000 description 107
- 235000010233 benzoic acid Nutrition 0.000 description 103
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 96
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 90
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 78
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
- 238000000354 decomposition reaction Methods 0.000 description 35
- 238000002360 preparation method Methods 0.000 description 31
- 239000011343 solid material Substances 0.000 description 30
- 238000002156 mixing Methods 0.000 description 29
- 239000007858 starting material Substances 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 238000009835 boiling Methods 0.000 description 26
- 238000003756 stirring Methods 0.000 description 25
- 239000002253 acid Substances 0.000 description 23
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 20
- 238000001953 recrystallisation Methods 0.000 description 19
- 229940086542 triethylamine Drugs 0.000 description 19
- DDMPIPCSFLSDEX-UHFFFAOYSA-N 3h-benzimidazole-5-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=C2N=CNC2=C1 DDMPIPCSFLSDEX-UHFFFAOYSA-N 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 17
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 17
- 229960000583 acetic acid Drugs 0.000 description 15
- 239000003610 charcoal Substances 0.000 description 15
- 239000003208 petroleum Substances 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 14
- 239000012362 glacial acetic acid Substances 0.000 description 13
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 10
- 210000002966 serum Anatomy 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 235000012000 cholesterol Nutrition 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 229940088710 antibiotic agent Drugs 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- KXXBWCHZAIJNKI-UHFFFAOYSA-N O.N1=CNC2=C1C=CC(=C2)C(=O)O Chemical compound O.N1=CNC2=C1C=CC(=C2)C(=O)O KXXBWCHZAIJNKI-UHFFFAOYSA-N 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 235000005911 diet Nutrition 0.000 description 5
- 230000037213 diet Effects 0.000 description 5
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- 159000000000 sodium salts Chemical class 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- QBXLEWZGGBRPEO-UHFFFAOYSA-N 3H-benzimidazole-5-carbonyl chloride hydrochloride Chemical compound Cl.ClC(=O)C1=CC=C2NC=NC2=C1 QBXLEWZGGBRPEO-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
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- 239000003480 eluent Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000011872 intimate mixture Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 150000004682 monohydrates Chemical class 0.000 description 4
- BASNZTUXPUAQLZ-UHFFFAOYSA-N nonadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCC(Cl)=O BASNZTUXPUAQLZ-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
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- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 1
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- 150000002895 organic esters Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- PQZWQGNQOVDTRF-UHFFFAOYSA-N pentadecanoyl chloride Chemical compound CCCCCCCCCCCCCCC(Cl)=O PQZWQGNQOVDTRF-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
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- HPOKESDSMZRZLC-UHFFFAOYSA-N propan-2-one;hydrochloride Chemical compound Cl.CC(C)=O HPOKESDSMZRZLC-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7922011 | 1979-06-25 | ||
| GB7922011 | 1979-06-25 | ||
| GB8013948 | 1980-04-28 | ||
| GB8013948 | 1980-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8003627A true NL8003627A (nl) | 1980-12-30 |
Family
ID=26271953
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8003627A NL8003627A (nl) | 1979-06-25 | 1980-06-23 | Benzimidazoolderivaten alsmede farmaceutische preparaten en werkwijze voor het bereiden daarvan. |
| NL8003628A NL8003628A (nl) | 1979-06-25 | 1980-06-23 | Acylaminobenzoeezuurderivaten, farmaceutische preparaten alsmede werkwijze voor het bereiden daarvan. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8003628A NL8003628A (nl) | 1979-06-25 | 1980-06-23 | Acylaminobenzoeezuurderivaten, farmaceutische preparaten alsmede werkwijze voor het bereiden daarvan. |
Country Status (20)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5476849A (en) * | 1984-03-19 | 1995-12-19 | The Rockefeller University | Methods for glycosylation inhibition using amino-benzoic acids and derivatives |
| US5514676A (en) * | 1984-03-19 | 1996-05-07 | The Rockefeller University | Amino-benzoic acids and derivatives, and methods of use |
| US4716175A (en) * | 1987-02-24 | 1987-12-29 | Warner-Lambert Company | Saturated fatty acid amides as inhibitors of acyl-CoA:cholesterol acyltransferase |
| WO1992002216A1 (en) * | 1990-08-01 | 1992-02-20 | Univ Rockefeller | Advanced glycation inhibitors containing amino-benzoic acids and derivatives, and methods of use |
| GB2498922A (en) * | 2011-12-14 | 2013-08-07 | Madison Filter 981 Ltd | Antistatic link belt |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH260770D (enrdf_load_stackoverflow) * | 1969-02-25 | |||
| DE1948795A1 (de) * | 1969-09-26 | 1971-04-08 | Rhein Chemie Rheinau Gmbh | 4,5,6,7-Tetrahydrobenzimidazole,Verfahren zu ihrer Herstellung und ihre Verwendung als Korrosionsinhibitoren und Alterungsschutzmittel |
-
1980
- 1980-06-21 GR GR62276A patent/GR69291B/el unknown
- 1980-06-21 GR GR62277A patent/GR69292B/el unknown
- 1980-06-23 AU AU59545/80A patent/AU5954580A/en not_active Abandoned
- 1980-06-23 NO NO801875A patent/NO801875L/no unknown
- 1980-06-23 DE DE19803023433 patent/DE3023433A1/de not_active Withdrawn
- 1980-06-23 NZ NZ194123A patent/NZ194123A/xx unknown
- 1980-06-23 NL NL8003627A patent/NL8003627A/nl not_active Application Discontinuation
- 1980-06-23 IL IL60378A patent/IL60378A0/xx unknown
- 1980-06-23 DE DE19803023432 patent/DE3023432A1/de not_active Withdrawn
- 1980-06-23 PH PH24182A patent/PH15713A/en unknown
- 1980-06-23 AU AU59546/80A patent/AU5954680A/en not_active Abandoned
- 1980-06-23 CA CA000354555A patent/CA1141765A/en not_active Expired
- 1980-06-23 NZ NZ194122A patent/NZ194122A/xx unknown
- 1980-06-23 NL NL8003628A patent/NL8003628A/nl not_active Application Discontinuation
- 1980-06-23 SE SE8004621A patent/SE8004621L/xx not_active Application Discontinuation
- 1980-06-23 PT PT71445A patent/PT71445A/pt unknown
- 1980-06-23 DK DK268080A patent/DK268080A/da not_active Application Discontinuation
- 1980-06-23 NO NO801876A patent/NO801876L/no unknown
- 1980-06-23 YU YU01636/80A patent/YU163680A/xx unknown
- 1980-06-23 IT IT22966/80A patent/IT1131841B/it active
- 1980-06-23 IL IL60379A patent/IL60379A0/xx unknown
- 1980-06-23 FR FR8013846A patent/FR2459794A1/fr not_active Withdrawn
- 1980-06-23 ES ES492692A patent/ES492692A0/es active Granted
- 1980-06-23 FI FI802009A patent/FI802009A7/fi not_active Application Discontinuation
- 1980-06-23 GB GB8020548A patent/GB2053912B/en not_active Expired
- 1980-06-23 IT IT22965/80A patent/IT1197459B/it active
- 1980-06-23 ES ES492693A patent/ES8105268A1/es not_active Expired
- 1980-06-23 AT AT0328780A patent/ATA328780A/de not_active Application Discontinuation
- 1980-06-23 PT PT71444A patent/PT71444A/pt unknown
- 1980-06-23 SE SE8004622A patent/SE8004622L/xx not_active Application Discontinuation
- 1980-06-23 FR FR8013845A patent/FR2459796A1/fr not_active Withdrawn
- 1980-06-23 DK DK267880A patent/DK267880A/da not_active Application Discontinuation
- 1980-06-23 FI FI802008A patent/FI802008A7/fi not_active Application Discontinuation
- 1980-06-24 LU LU82546A patent/LU82546A1/fr unknown
- 1980-06-24 LU LU82545A patent/LU82545A1/fr unknown
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