NO801875L - Fremgangsmaate ved fremstilling av benzimidazolderivater - Google Patents
Fremgangsmaate ved fremstilling av benzimidazolderivaterInfo
- Publication number
- NO801875L NO801875L NO801875A NO801875A NO801875L NO 801875 L NO801875 L NO 801875L NO 801875 A NO801875 A NO 801875A NO 801875 A NO801875 A NO 801875A NO 801875 L NO801875 L NO 801875L
- Authority
- NO
- Norway
- Prior art keywords
- benzimidazole
- methyl
- carboxylic acid
- carboxylate
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 239000000203 mixture Substances 0.000 claims description 144
- 150000001875 compounds Chemical class 0.000 claims description 106
- -1 methyl 2-(n-heptyl)benzimidazole-5-carboxylate Chemical compound 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- 238000010992 reflux Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 150000001556 benzimidazoles Chemical class 0.000 claims description 7
- COYPLDIXZODDDL-UHFFFAOYSA-N 3h-benzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=CNC2=C1 COYPLDIXZODDDL-UHFFFAOYSA-N 0.000 claims description 5
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 4
- 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 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 3
- 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 2
- ORVPLAVHXHCROP-UHFFFAOYSA-N 2-tridecan-3-yl-3H-benzimidazole-5-carboxylic acid Chemical compound CCC(CCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O ORVPLAVHXHCROP-UHFFFAOYSA-N 0.000 claims description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- QZTJWLFUDRRLCU-UHFFFAOYSA-N 2-tridecyl-3H-benzimidazole-5-carboxylic acid Chemical compound C(CCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O QZTJWLFUDRRLCU-UHFFFAOYSA-N 0.000 claims 2
- OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 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
- UUQJTYOJAAORQY-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethyl 2-pentadecyl-3H-benzimidazole-5-carboxylate Chemical compound C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)OCOC(C(C)(C)C)=O UUQJTYOJAAORQY-UHFFFAOYSA-N 0.000 claims 1
- NIHPGICHMPNPHW-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-pentadecyl-3H-benzimidazole-5-carboxylate Chemical compound C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)OCC(CO)O NIHPGICHMPNPHW-UHFFFAOYSA-N 0.000 claims 1
- YETLXJLMQXGLHM-UHFFFAOYSA-N 2-decyl-3H-benzimidazole-5-carboxylic acid Chemical compound C(CCCCCCCCC)C=1NC2=C(N=1)C=CC(=C2)C(=O)O YETLXJLMQXGLHM-UHFFFAOYSA-N 0.000 claims 1
- QGFGLYOMJKJZIC-UHFFFAOYSA-N 2-dodecyl-1h-benzimidazole Chemical compound C1=CC=C2NC(CCCCCCCCCCCC)=NC2=C1 QGFGLYOMJKJZIC-UHFFFAOYSA-N 0.000 claims 1
- TVFUKKLDYCDOLF-UHFFFAOYSA-N 2-dodecyl-4-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(CCCCCCCCCCCC)=NC2=C1C TVFUKKLDYCDOLF-UHFFFAOYSA-N 0.000 claims 1
- ZIQWGKZMLONEBR-UHFFFAOYSA-N 2-heptadecyl-3H-benzimidazole-5-carboxylic acid Chemical compound C(CCCCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O ZIQWGKZMLONEBR-UHFFFAOYSA-N 0.000 claims 1
- NKZFTPGFPASHBV-UHFFFAOYSA-N 2-heptyl-3h-benzimidazole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2NC(CCCCCCC)=NC2=C1 NKZFTPGFPASHBV-UHFFFAOYSA-N 0.000 claims 1
- WFFOXZUCRUTSQP-UHFFFAOYSA-N 2-hexadecyl-3H-benzimidazole-5-carboxylic acid Chemical compound C(CCCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O WFFOXZUCRUTSQP-UHFFFAOYSA-N 0.000 claims 1
- HACWHGXFSQIXGG-UHFFFAOYSA-N 2-icosyl-3H-benzimidazole-5-carboxylic acid Chemical compound C(CCCCCCCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O HACWHGXFSQIXGG-UHFFFAOYSA-N 0.000 claims 1
- OFVZUKRCHSRBFN-UHFFFAOYSA-N 2-nonadecyl-3H-benzimidazole-5-carboxylic acid Chemical compound C(CCCCCCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O OFVZUKRCHSRBFN-UHFFFAOYSA-N 0.000 claims 1
- GMBJQUCFSAGJNO-UHFFFAOYSA-N 2-nonyl-3h-benzimidazole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2NC(CCCCCCCCC)=NC2=C1 GMBJQUCFSAGJNO-UHFFFAOYSA-N 0.000 claims 1
- YLIPWEOUPRQKRE-UHFFFAOYSA-N 2-octadecyl-3H-benzimidazole-5-carboxylic acid Chemical compound C(CCCCCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O YLIPWEOUPRQKRE-UHFFFAOYSA-N 0.000 claims 1
- IXXUVMLJTPMKJI-UHFFFAOYSA-N 2-tetradecyl-3H-benzimidazole-5-carboxylic acid Chemical compound C(CCCCCCCCCCCCC)C=1NC2=C(N=1)C=CC(=C2)C(=O)O IXXUVMLJTPMKJI-UHFFFAOYSA-N 0.000 claims 1
- PYLJZIFACMOPAS-UHFFFAOYSA-N 2-tridecan-5-yl-3H-benzimidazole-5-carboxylic acid Chemical compound CCCCC(CCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O PYLJZIFACMOPAS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- WKWALHSUNLUEBL-UHFFFAOYSA-N butyl 2-pentadecyl-3H-benzimidazole-5-carboxylate Chemical compound C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)OCCCC WKWALHSUNLUEBL-UHFFFAOYSA-N 0.000 claims 1
- PIVJIRIXQFUFJM-UHFFFAOYSA-N hexyl 2-pentadecyl-3H-benzimidazole-5-carboxylate Chemical compound C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)OCCCCCC PIVJIRIXQFUFJM-UHFFFAOYSA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- BSTLQHQHZPKFTC-UHFFFAOYSA-N methyl 2-decyl-3H-benzimidazole-5-carboxylate Chemical compound C(CCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)OC BSTLQHQHZPKFTC-UHFFFAOYSA-N 0.000 claims 1
- AQZZCSCCSDQMBH-UHFFFAOYSA-N methyl 2-heptadecyl-3H-benzimidazole-5-carboxylate Chemical compound C(CCCCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)OC AQZZCSCCSDQMBH-UHFFFAOYSA-N 0.000 claims 1
- ODKWIBBMDZIUPQ-UHFFFAOYSA-N methyl 2-hexadecyl-3H-benzimidazole-5-carboxylate Chemical compound C(CCCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)OC ODKWIBBMDZIUPQ-UHFFFAOYSA-N 0.000 claims 1
- DDSTXKWPXFUFCW-UHFFFAOYSA-N methyl 2-nonadecyl-3H-benzimidazole-5-carboxylate Chemical compound C(CCCCCCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)OC DDSTXKWPXFUFCW-UHFFFAOYSA-N 0.000 claims 1
- IPITWMFHXAFWJZ-UHFFFAOYSA-N methyl 2-octadecyl-3H-benzimidazole-5-carboxylate Chemical compound C(CCCCCCCCCCCCCCCCC)C=1NC2=C(N=1)C=CC(=C2)C(=O)OC IPITWMFHXAFWJZ-UHFFFAOYSA-N 0.000 claims 1
- MYUJJQIQDAILMF-UHFFFAOYSA-N propan-2-yl 2-pentadecyl-3H-benzimidazole-5-carboxylate Chemical compound C(CCCCCCCCCCCCCC)C=1NC2=C(N=1)C=CC(=C2)C(=O)OC(C)C MYUJJQIQDAILMF-UHFFFAOYSA-N 0.000 claims 1
- YNDLZNTYWDQTSR-UHFFFAOYSA-N tert-butyl 2-pentadecyl-3H-benzimidazole-5-carboxylate Chemical compound C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)OC(C)(C)C YNDLZNTYWDQTSR-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 description 204
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 149
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
- 239000000243 solution Substances 0.000 description 120
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 101
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 85
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 72
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 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 38
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 34
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 238000000354 decomposition reaction Methods 0.000 description 25
- 239000007858 starting material Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 20
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- 238000001953 recrystallisation Methods 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- 238000009835 boiling Methods 0.000 description 18
- IOPLHGOSNCJOOO-UHFFFAOYSA-N methyl 3,4-diaminobenzoate Chemical compound COC(=O)C1=CC=C(N)C(N)=C1 IOPLHGOSNCJOOO-UHFFFAOYSA-N 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 17
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- 239000012362 glacial acetic acid Substances 0.000 description 15
- 239000003208 petroleum Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 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 14
- 239000000706 filtrate Substances 0.000 description 13
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 12
- 239000005711 Benzoic acid Substances 0.000 description 11
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- GIWQIAFBONKYOM-UHFFFAOYSA-N Cl.C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O Chemical compound Cl.C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O GIWQIAFBONKYOM-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 235000010233 benzoic acid Nutrition 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- TVURZCDPXALPLA-UHFFFAOYSA-N 3,4-bis(dodecanoylamino)benzoic acid Chemical compound C(CCCCCCCCCCC)(=O)NC=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCC)=O TVURZCDPXALPLA-UHFFFAOYSA-N 0.000 description 7
- 238000003776 cleavage reaction Methods 0.000 description 7
- 235000005911 diet Nutrition 0.000 description 7
- 230000037213 diet Effects 0.000 description 7
- ADQCGQPQICIRLP-UHFFFAOYSA-N methyl 3,4-bis(hexadecanoylamino)benzoate Chemical compound C(CCCCCCCCCCCCCCC)(=O)NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCCCCCCCCCC)=O ADQCGQPQICIRLP-UHFFFAOYSA-N 0.000 description 7
- 230000007017 scission Effects 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- CPEFAORKRPDVLS-UHFFFAOYSA-N methyl 4-amino-3-(hexadecanoylamino)benzoate Chemical compound NC1=C(C=C(C(=O)OC)C=C1)NC(CCCCCCCCCCCCCCC)=O CPEFAORKRPDVLS-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ZRUIDXRFXLHRSM-UHFFFAOYSA-N 3,4-bis(hexadecanoylamino)benzoic acid Chemical compound C(CCCCCCCCCCCCCCC)(=O)NC=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCCCCCC)=O ZRUIDXRFXLHRSM-UHFFFAOYSA-N 0.000 description 5
- POIVSXODMPVBGX-UHFFFAOYSA-N Cl.C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)Cl Chemical compound Cl.C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)Cl POIVSXODMPVBGX-UHFFFAOYSA-N 0.000 description 5
- 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
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 206010012601 diabetes mellitus Diseases 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- CZBKGPBHXLKFFY-UHFFFAOYSA-N methyl 4-amino-3-(octanoylamino)benzoate Chemical compound NC1=C(C=C(C(=O)OC)C=C1)NC(CCCCCCC)=O CZBKGPBHXLKFFY-UHFFFAOYSA-N 0.000 description 5
- LPWCRLGKYWVLHQ-UHFFFAOYSA-N tetradecanoyl chloride Chemical compound CCCCCCCCCCCCCC(Cl)=O LPWCRLGKYWVLHQ-UHFFFAOYSA-N 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- XCDJRGBDKUNZSP-UHFFFAOYSA-N 4-amino-3-(nonadecanoylamino)benzoic acid Chemical compound NC1=C(C=C(C(=O)O)C=C1)NC(CCCCCCCCCCCCCCCCCC)=O XCDJRGBDKUNZSP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- DUNWQUZDSJMPJU-UHFFFAOYSA-N Cl.C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)OC Chemical compound Cl.C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)OC DUNWQUZDSJMPJU-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MQTMHAZBGNBILJ-UHFFFAOYSA-N O.C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O Chemical compound O.C(CCCCCCCCCCCCCC)C=1NC2=C(N1)C=CC(=C2)C(=O)O MQTMHAZBGNBILJ-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
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- ZRRNYJOVBDYPJF-UHFFFAOYSA-N methyl 3-amino-4-(octanoylamino)benzoate Chemical compound NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCC)=O ZRRNYJOVBDYPJF-UHFFFAOYSA-N 0.000 description 1
- OLISWDUPUFSSSV-UHFFFAOYSA-N methyl 4-(decanoylamino)-3-nitrobenzoate Chemical compound C(CCCCCCCCC)(=O)NC1=C(C=C(C(=O)OC)C=C1)[N+](=O)[O-] OLISWDUPUFSSSV-UHFFFAOYSA-N 0.000 description 1
- LENHLWVEJRGINP-UHFFFAOYSA-N methyl 4-(hexadecanoylamino)-3-nitrobenzoate Chemical compound C(CCCCCCCCCCCCCCC)(=O)NC1=C(C=C(C(=O)OC)C=C1)[N+](=O)[O-] LENHLWVEJRGINP-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- VIJMMQUAJQEELS-UHFFFAOYSA-N n,n-bis(ethenyl)ethenamine Chemical compound C=CN(C=C)C=C VIJMMQUAJQEELS-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 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
- 239000004533 oil dispersion Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration 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
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 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
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect 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
- 230000009466 transformation Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- JUKPJGZUFHCZQI-UHFFFAOYSA-N undecanoyl chloride Chemical compound CCCCCCCCCCC(Cl)=O JUKPJGZUFHCZQI-UHFFFAOYSA-N 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 208000021331 vascular occlusion disease Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7922011 | 1979-06-25 | ||
| GB8013948 | 1980-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO801875L true NO801875L (no) | 1980-12-29 |
Family
ID=26271953
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801875A NO801875L (no) | 1979-06-25 | 1980-06-23 | Fremgangsmaate ved fremstilling av benzimidazolderivater |
| NO801876A NO801876L (no) | 1979-06-25 | 1980-06-23 | Fremgangsmaate ved fremstilling av acylaminobenzosyrederivater |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801876A NO801876L (no) | 1979-06-25 | 1980-06-23 | Fremgangsmaate ved fremstilling av acylaminobenzosyrederivater |
Country Status (20)
| Country | Link |
|---|---|
| AT (1) | ATA328780A (de) |
| AU (2) | AU5954580A (de) |
| CA (1) | CA1141765A (de) |
| DE (2) | DE3023433A1 (de) |
| DK (2) | DK268080A (de) |
| ES (2) | ES492693A0 (de) |
| FI (2) | FI802009A (de) |
| FR (2) | FR2459796A1 (de) |
| GB (1) | GB2053912B (de) |
| GR (2) | GR69291B (de) |
| IL (2) | IL60379A0 (de) |
| IT (2) | IT1197459B (de) |
| LU (2) | LU82546A1 (de) |
| NL (2) | NL8003627A (de) |
| NO (2) | NO801875L (de) |
| NZ (2) | NZ194123A (de) |
| PH (1) | PH15713A (de) |
| PT (2) | PT71445A (de) |
| SE (2) | SE8004621L (de) |
| YU (1) | YU163680A (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5514676A (en) * | 1984-03-19 | 1996-05-07 | The Rockefeller University | Amino-benzoic acids and derivatives, and methods of use |
| US5476849A (en) * | 1984-03-19 | 1995-12-19 | The Rockefeller University | Methods for glycosylation inhibition using amino-benzoic acids and derivatives |
| US4716175A (en) * | 1987-02-24 | 1987-12-29 | Warner-Lambert Company | Saturated fatty acid amides as inhibitors of acyl-CoA:cholesterol acyltransferase |
| 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 (de) * | 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 AT AT0328780A patent/ATA328780A/de not_active Application Discontinuation
- 1980-06-23 DE DE19803023433 patent/DE3023433A1/de not_active Withdrawn
- 1980-06-23 ES ES492693A patent/ES492693A0/es active Granted
- 1980-06-23 IT IT22965/80A patent/IT1197459B/it active
- 1980-06-23 PT PT71445A patent/PT71445A/pt unknown
- 1980-06-23 NZ NZ194123A patent/NZ194123A/xx unknown
- 1980-06-23 FI FI802009A patent/FI802009A/fi not_active Application Discontinuation
- 1980-06-23 DK DK268080A patent/DK268080A/da not_active Application Discontinuation
- 1980-06-23 CA CA000354555A patent/CA1141765A/en not_active Expired
- 1980-06-23 YU YU01636/80A patent/YU163680A/xx unknown
- 1980-06-23 DE DE19803023432 patent/DE3023432A1/de not_active Withdrawn
- 1980-06-23 SE SE8004621A patent/SE8004621L/xx not_active Application Discontinuation
- 1980-06-23 NL NL8003627A patent/NL8003627A/nl not_active Application Discontinuation
- 1980-06-23 SE SE8004622A patent/SE8004622L/xx not_active Application Discontinuation
- 1980-06-23 IT IT22966/80A patent/IT1131841B/it active
- 1980-06-23 PT PT71444A patent/PT71444A/pt unknown
- 1980-06-23 FI FI802008A patent/FI802008A/fi not_active Application Discontinuation
- 1980-06-23 NO NO801875A patent/NO801875L/no unknown
- 1980-06-23 FR FR8013845A patent/FR2459796A1/fr not_active Withdrawn
- 1980-06-23 NO NO801876A patent/NO801876L/no unknown
- 1980-06-23 ES ES492692A patent/ES492692A0/es active Granted
- 1980-06-23 NL NL8003628A patent/NL8003628A/nl not_active Application Discontinuation
- 1980-06-23 FR FR8013846A patent/FR2459794A1/fr not_active Withdrawn
- 1980-06-23 PH PH24182A patent/PH15713A/en unknown
- 1980-06-23 IL IL60379A patent/IL60379A0/xx unknown
- 1980-06-23 DK DK267880A patent/DK267880A/da not_active Application Discontinuation
- 1980-06-23 IL IL60378A patent/IL60378A0/xx unknown
- 1980-06-23 NZ NZ194122A patent/NZ194122A/xx unknown
- 1980-06-23 AU AU59546/80A patent/AU5954680A/en not_active Abandoned
- 1980-06-23 GB GB8020548A patent/GB2053912B/en not_active Expired
- 1980-06-24 LU LU82546A patent/LU82546A1/fr unknown
- 1980-06-24 LU LU82545A patent/LU82545A1/fr unknown
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