NO801876L - Fremgangsmaate ved fremstilling av acylaminobenzosyrederivater - Google Patents
Fremgangsmaate ved fremstilling av acylaminobenzosyrederivaterInfo
- Publication number
- NO801876L NO801876L NO801876A NO801876A NO801876L NO 801876 L NO801876 L NO 801876L NO 801876 A NO801876 A NO 801876A NO 801876 A NO801876 A NO 801876A NO 801876 L NO801876 L NO 801876L
- Authority
- NO
- Norway
- Prior art keywords
- amino
- methyl
- bis
- benzoic acid
- benzoate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 239000002253 acid Substances 0.000 title claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 30
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- -1 methyl 3-amino-4-(n-hexadecanamido)-benzoate Chemical compound 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000005711 Benzoic acid Substances 0.000 claims description 10
- 235000010233 benzoic acid Nutrition 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 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 claims 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 claims description 7
- 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 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 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 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 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 claims description 4
- USRUOUQUSROHCU-UHFFFAOYSA-N 3-amino-4-(octanoylamino)benzoic acid Chemical compound CCCCCCCC(=O)NC1=CC=C(C(O)=O)C=C1N USRUOUQUSROHCU-UHFFFAOYSA-N 0.000 claims description 3
- FXGGWISCHMSUBZ-UHFFFAOYSA-N 4-amino-3-(hexadecanoylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)NC1=CC(C(O)=O)=CC=C1N FXGGWISCHMSUBZ-UHFFFAOYSA-N 0.000 claims description 3
- SSLPEZYAXOTFGH-UHFFFAOYSA-N methyl 3-amino-4-(dodecanoylamino)benzoate Chemical compound NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCCCCCC)=O SSLPEZYAXOTFGH-UHFFFAOYSA-N 0.000 claims description 3
- MQILNHFIIYCJLX-UHFFFAOYSA-N methyl 4-amino-3-(dodecanoylamino)benzoate Chemical compound NC1=C(C=C(C(=O)OC)C=C1)NC(CCCCCCCCCCC)=O MQILNHFIIYCJLX-UHFFFAOYSA-N 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- XPJMIIKQWALGDM-UHFFFAOYSA-N 2,3-bis(hexadecanoylamino)benzoic acid Chemical compound C(CCCCCCCCCCCCCCC)(=O)NC1=C(C(=O)O)C=CC=C1NC(CCCCCCCCCCCCCCC)=O XPJMIIKQWALGDM-UHFFFAOYSA-N 0.000 claims description 2
- FHSSLCMPKIIGAZ-UHFFFAOYSA-N 3,4-bis(2-methyltetradecanoylamino)benzoic acid Chemical compound CC(C(=O)NC=1C=C(C(=O)O)C=CC1NC(C(CCCCCCCCCCCC)C)=O)CCCCCCCCCCCC FHSSLCMPKIIGAZ-UHFFFAOYSA-N 0.000 claims description 2
- YJKBVLMUBNZHFC-UHFFFAOYSA-N 3,4-bis(heptadecanoylamino)benzoic acid Chemical compound C(CCCCCCCCCCCCCCCC)(=O)NC=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCCCCCCC)=O YJKBVLMUBNZHFC-UHFFFAOYSA-N 0.000 claims description 2
- MKRQDSWZGMWFCC-UHFFFAOYSA-N 3,4-bis(octanoylamino)benzoic acid Chemical compound C(CCCCCCC)(=O)NC=1C=C(C(=O)O)C=CC1NC(CCCCCCC)=O MKRQDSWZGMWFCC-UHFFFAOYSA-N 0.000 claims description 2
- ZUYZVYRKLUGCGQ-UHFFFAOYSA-N 3,4-bis(pentadecanoylamino)benzoic acid Chemical compound C(CCCCCCCCCCCCCC)(=O)NC=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCCCCC)=O ZUYZVYRKLUGCGQ-UHFFFAOYSA-N 0.000 claims description 2
- GNOVTWKUAZOMRO-UHFFFAOYSA-N 3,4-bis(tetradecanoylamino)benzoic acid Chemical compound C(CCCCCCCCCCCCC)(=O)NC=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCCCC)=O GNOVTWKUAZOMRO-UHFFFAOYSA-N 0.000 claims description 2
- JPGXSKJZQNPWKW-UHFFFAOYSA-N 3-amino-4-(dodecanoylamino)benzoic acid Chemical compound NC=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCC)=O JPGXSKJZQNPWKW-UHFFFAOYSA-N 0.000 claims description 2
- DJDWARKOQNKMDE-UHFFFAOYSA-N 4-amino-3-(2-butyldecanoylamino)benzoic acid Chemical compound NC1=C(C=C(C(=O)O)C=C1)NC(C(CCCCCCCC)CCCC)=O DJDWARKOQNKMDE-UHFFFAOYSA-N 0.000 claims description 2
- PTRSAFYCKWKOCG-UHFFFAOYSA-N 4-amino-3-(2-hexyloctanoylamino)benzoic acid Chemical compound NC1=C(C=C(C(=O)O)C=C1)NC(C(CCCCCC)CCCCCC)=O PTRSAFYCKWKOCG-UHFFFAOYSA-N 0.000 claims description 2
- RRUMRKDJQRDZLU-UHFFFAOYSA-N 4-amino-3-(octadecanoylamino)benzoic acid Chemical compound NC1=C(C=C(C(=O)O)C=C1)NC(CCCCCCCCCCCCCCCCC)=O RRUMRKDJQRDZLU-UHFFFAOYSA-N 0.000 claims description 2
- WAPNJCNNOJKVSC-UHFFFAOYSA-N 4-amino-3-(octanoylamino)benzoic acid Chemical compound NC1=C(C=C(C(=O)O)C=C1)NC(CCCCCCC)=O WAPNJCNNOJKVSC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- ODOFMBQBTBBYSC-UHFFFAOYSA-N methyl 3,4-bis(decanoylamino)benzoate Chemical compound C(CCCCCCCCC)(=O)NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCCCC)=O ODOFMBQBTBBYSC-UHFFFAOYSA-N 0.000 claims description 2
- IFBYDKXBCOLHEB-UHFFFAOYSA-N methyl 3,4-bis(dodecanoylamino)benzoate Chemical compound C(CCCCCCCCCCC)(=O)NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCCCCCC)=O IFBYDKXBCOLHEB-UHFFFAOYSA-N 0.000 claims description 2
- HNXDMCSUQRQHPU-UHFFFAOYSA-N methyl 3,4-bis(nonanoylamino)benzoate Chemical compound C(CCCCCCCC)(=O)NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCCC)=O HNXDMCSUQRQHPU-UHFFFAOYSA-N 0.000 claims description 2
- XRGNTSBWCWKRHM-UHFFFAOYSA-N methyl 3,4-bis(octadecanoylamino)benzoate Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCCCCCCCCCCCC)=O XRGNTSBWCWKRHM-UHFFFAOYSA-N 0.000 claims description 2
- PCXGEMVDECEVTI-UHFFFAOYSA-N methyl 3,4-bis(tetradecanoylamino)benzoate Chemical compound C(CCCCCCCCCCCCC)(=O)NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCCCCCCCC)=O PCXGEMVDECEVTI-UHFFFAOYSA-N 0.000 claims description 2
- AYKBVSFZTBGFTQ-UHFFFAOYSA-N methyl 3,4-bis(tridecanoylamino)benzoate Chemical compound C(CCCCCCCCCCCC)(=O)NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCCCCCCC)=O AYKBVSFZTBGFTQ-UHFFFAOYSA-N 0.000 claims description 2
- DJNKIZIEWZQCND-UHFFFAOYSA-N methyl 3,4-bis(undecanoylamino)benzoate Chemical compound C(CCCCCCCCCC)(=O)NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCCCCC)=O DJNKIZIEWZQCND-UHFFFAOYSA-N 0.000 claims description 2
- IAYPFKNIRXZCKE-UHFFFAOYSA-N methyl 3-amino-4-(decanoylamino)benzoate Chemical compound NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCCCC)=O IAYPFKNIRXZCKE-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- IWVZDAOAOLHVSE-UHFFFAOYSA-N methyl 4-amino-3-(tetradecanoylamino)benzoate Chemical compound NC1=C(C=C(C(=O)OC)C=C1)NC(CCCCCCCCCCCCC)=O IWVZDAOAOLHVSE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- BIKOFYYQYSBQKW-UHFFFAOYSA-N 3,4-bis(decanoylamino)benzoic acid Chemical compound C(CCCCCCCCC)(=O)NC=1C=C(C(=O)O)C=CC1NC(CCCCCCCCC)=O BIKOFYYQYSBQKW-UHFFFAOYSA-N 0.000 claims 1
- BEMHXKGOBDZVML-UHFFFAOYSA-N 3,4-bis(octadecanoylamino)benzoic acid Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)NC=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCCCCCCCC)=O BEMHXKGOBDZVML-UHFFFAOYSA-N 0.000 claims 1
- ZSWRAMQXHDNWQW-UHFFFAOYSA-N 4-amino-3-(2-ethyldodecanoylamino)benzoic acid Chemical compound NC1=C(C=C(C(=O)O)C=C1)NC(C(CCCCCCCCCC)CC)=O ZSWRAMQXHDNWQW-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- SVOXRUJDYNKQRO-UHFFFAOYSA-N methyl 4-amino-3-(tridecanoylamino)benzoate Chemical compound NC1=C(C=C(C(=O)OC)C=C1)NC(CCCCCCCCCCCC)=O SVOXRUJDYNKQRO-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 description 84
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 78
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 53
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 238000001953 recrystallisation Methods 0.000 description 19
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 16
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 13
- 239000012894 fetal calf serum Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 12
- 239000012362 glacial acetic acid Substances 0.000 description 11
- IOPLHGOSNCJOOO-UHFFFAOYSA-N methyl 3,4-diaminobenzoate Chemical compound COC(=O)C1=CC=C(N)C(N)=C1 IOPLHGOSNCJOOO-UHFFFAOYSA-N 0.000 description 11
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000003242 anti bacterial agent Substances 0.000 description 7
- 229940088710 antibiotic agent Drugs 0.000 description 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- VANIXZJNMJJWGE-UHFFFAOYSA-N methyl 4-(dodecanoylamino)-3-nitrobenzoate Chemical compound C(CCCCCCCCCCC)(=O)NC1=C(C=C(C(=O)OC)C=C1)[N+](=O)[O-] VANIXZJNMJJWGE-UHFFFAOYSA-N 0.000 description 4
- 239000003226 mitogen Substances 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
- 238000007363 ring formation reaction Methods 0.000 description 4
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 4
- 239000008247 solid mixture Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- LPWCRLGKYWVLHQ-UHFFFAOYSA-N tetradecanoyl chloride Chemical compound CCCCCCCCCCCCCC(Cl)=O LPWCRLGKYWVLHQ-UHFFFAOYSA-N 0.000 description 4
- FJRPWCNFWGBGOF-UHFFFAOYSA-N tridecanoyl chloride Chemical compound CCCCCCCCCCCCC(Cl)=O FJRPWCNFWGBGOF-UHFFFAOYSA-N 0.000 description 4
- CYBJTIAYHLCKRR-UHFFFAOYSA-N 3-nitro-4-(octanoylamino)benzoic acid Chemical compound [N+](=O)([O-])C=1C=C(C(=O)O)C=CC1NC(CCCCCCC)=O CYBJTIAYHLCKRR-UHFFFAOYSA-N 0.000 description 3
- KHPJOVYNDNRHSO-UHFFFAOYSA-N 4-(hexadecanoylamino)-3-nitrobenzoic acid Chemical compound [N+](=O)([O-])C=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCCCCCC)=O KHPJOVYNDNRHSO-UHFFFAOYSA-N 0.000 description 3
- ZZNAYFWAXZJITH-UHFFFAOYSA-N 4-amino-3-nitrobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1[N+]([O-])=O ZZNAYFWAXZJITH-UHFFFAOYSA-N 0.000 description 3
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- 238000011534 incubation Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- HNTLUEZVPLRQEV-UHFFFAOYSA-N methyl 4-amino-3-nitrobenzoate Chemical compound COC(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 HNTLUEZVPLRQEV-UHFFFAOYSA-N 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 3
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- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
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- 208000018262 Peripheral vascular disease Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
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- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 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
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- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
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- PQZWQGNQOVDTRF-UHFFFAOYSA-N pentadecanoyl chloride Chemical compound CCCCCCCCCCCCCCC(Cl)=O PQZWQGNQOVDTRF-UHFFFAOYSA-N 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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 |
|---|---|
| NO801876L true NO801876L (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 Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801875A NO801875L (no) | 1979-06-25 | 1980-06-23 | Fremgangsmaate ved fremstilling av benzimidazolderivater |
Country Status (20)
| Country | Link |
|---|---|
| AT (1) | ATA328780A (it) |
| AU (2) | AU5954680A (it) |
| CA (1) | CA1141765A (it) |
| DE (2) | DE3023433A1 (it) |
| DK (2) | DK268080A (it) |
| ES (2) | ES492692A0 (it) |
| FI (2) | FI802009A (it) |
| FR (2) | FR2459796A1 (it) |
| GB (1) | GB2053912B (it) |
| GR (2) | GR69292B (it) |
| IL (2) | IL60378A0 (it) |
| IT (2) | IT1197459B (it) |
| LU (2) | LU82546A1 (it) |
| NL (2) | NL8003627A (it) |
| NO (2) | NO801875L (it) |
| NZ (2) | NZ194123A (it) |
| PH (1) | PH15713A (it) |
| PT (2) | PT71444A (it) |
| SE (2) | SE8004622L (it) |
| YU (1) | YU163680A (it) |
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 (it) * | 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 GR62277A patent/GR69292B/el unknown
- 1980-06-21 GR GR62276A patent/GR69291B/el unknown
- 1980-06-23 NO NO801875A patent/NO801875L/no unknown
- 1980-06-23 ES ES492692A patent/ES492692A0/es active Granted
- 1980-06-23 DK DK268080A patent/DK268080A/da not_active Application Discontinuation
- 1980-06-23 YU YU01636/80A patent/YU163680A/xx unknown
- 1980-06-23 PT PT71444A patent/PT71444A/pt unknown
- 1980-06-23 PT PT71445A patent/PT71445A/pt unknown
- 1980-06-23 DE DE19803023433 patent/DE3023433A1/de not_active Withdrawn
- 1980-06-23 FI FI802009A patent/FI802009A/fi not_active Application Discontinuation
- 1980-06-23 FR FR8013845A patent/FR2459796A1/fr not_active Withdrawn
- 1980-06-23 AU AU59546/80A patent/AU5954680A/en not_active Abandoned
- 1980-06-23 GB GB8020548A patent/GB2053912B/en not_active Expired
- 1980-06-23 ES ES492693A patent/ES492693A0/es active Granted
- 1980-06-23 NZ NZ194123A patent/NZ194123A/xx unknown
- 1980-06-23 SE SE8004622A patent/SE8004622L/xx not_active Application Discontinuation
- 1980-06-23 NZ NZ194122A patent/NZ194122A/xx unknown
- 1980-06-23 CA CA000354555A patent/CA1141765A/en not_active Expired
- 1980-06-23 SE SE8004621A patent/SE8004621L/xx not_active Application Discontinuation
- 1980-06-23 AU AU59545/80A patent/AU5954580A/en not_active Abandoned
- 1980-06-23 FI FI802008A patent/FI802008A/fi not_active Application Discontinuation
- 1980-06-23 NL NL8003627A patent/NL8003627A/nl not_active Application Discontinuation
- 1980-06-23 NO NO801876A patent/NO801876L/no unknown
- 1980-06-23 FR FR8013846A patent/FR2459794A1/fr not_active Withdrawn
- 1980-06-23 IL IL60378A patent/IL60378A0/xx unknown
- 1980-06-23 IT IT22965/80A patent/IT1197459B/it active
- 1980-06-23 IL IL60379A patent/IL60379A0/xx unknown
- 1980-06-23 NL NL8003628A patent/NL8003628A/nl not_active Application Discontinuation
- 1980-06-23 PH PH24182A patent/PH15713A/en unknown
- 1980-06-23 DE DE19803023432 patent/DE3023432A1/de not_active Withdrawn
- 1980-06-23 AT AT0328780A patent/ATA328780A/de not_active Application Discontinuation
- 1980-06-23 DK DK267880A patent/DK267880A/da not_active Application Discontinuation
- 1980-06-23 IT IT22966/80A patent/IT1131841B/it active
- 1980-06-24 LU LU82546A patent/LU82546A1/fr unknown
- 1980-06-24 LU LU82545A patent/LU82545A1/fr unknown
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