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
- 241001465754 Metazoa Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001266 acyl halides Chemical class 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 230000003516 hyperlipidaemic effect Effects 0.000 description 3
- 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
- 239000000047 product Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000007306 turnover Effects 0.000 description 3
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 2
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 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 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- RJECHNNFRHZQKU-UHFFFAOYSA-N Oelsaeurecholesterylester Natural products C12CCC3(C)C(C(C)CCCC(C)C)CCC3C2CC=C2C1(C)CCC(OC(=O)CCCCCCCC=CCCCCCCCC)C2 RJECHNNFRHZQKU-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 208000018262 Peripheral vascular disease Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 206010052779 Transplant rejections Diseases 0.000 description 2
- 206010053648 Vascular occlusion Diseases 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 210000003433 aortic smooth muscle cell Anatomy 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- RJECHNNFRHZQKU-RMUVNZEASA-N cholesteryl oleate Chemical compound C([C@@H]12)C[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)C1 RJECHNNFRHZQKU-RMUVNZEASA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 208000026278 immune system disease Diseases 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 210000001165 lymph node Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- PSCWPFDVVHFWAP-UHFFFAOYSA-N methyl 3,4-bis(octanoylamino)benzoate Chemical compound C(CCCCCCC)(=O)NC=1C=C(C(=O)OC)C=CC1NC(CCCCCCC)=O PSCWPFDVVHFWAP-UHFFFAOYSA-N 0.000 description 2
- FJTCUCJLQBKEEN-UHFFFAOYSA-N methyl 4-amino-3-(decanoylamino)benzoate Chemical compound NC1=C(C=C(C(=O)OC)C=C1)NC(CCCCCCCCC)=O FJTCUCJLQBKEEN-UHFFFAOYSA-N 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229940049964 oleate Drugs 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 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 2
- 210000002966 serum Anatomy 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 208000021331 vascular occlusion disease Diseases 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical class OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
- QMHQRMYKISMXQZ-UHFFFAOYSA-N 2-(icosanoylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)NC1=CC=CC=C1C(O)=O QMHQRMYKISMXQZ-UHFFFAOYSA-N 0.000 description 1
- OALOLWZZSHLVTK-UHFFFAOYSA-N 2-ethyldodecanoyl chloride Chemical compound CCCCCCCCCCC(CC)C(Cl)=O OALOLWZZSHLVTK-UHFFFAOYSA-N 0.000 description 1
- HZPNSZFAYUWMBC-UHFFFAOYSA-N 2-hexyloctanoyl chloride Chemical compound CCCCCCC(C(Cl)=O)CCCCCC HZPNSZFAYUWMBC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- YAIHPSGLPLBMDD-UHFFFAOYSA-N 3,4-bis(henicosanoylamino)benzoic acid Chemical compound C(CCCCCCCCCCCCCCCCCCCC)(=O)NC=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCCCCCCCCCCC)=O YAIHPSGLPLBMDD-UHFFFAOYSA-N 0.000 description 1
- LJWHZRJHIQAQDD-UHFFFAOYSA-N 3,4-bis(tridecanoylamino)benzoic acid Chemical compound C(CCCCCCCCCCCC)(=O)NC=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCCC)=O LJWHZRJHIQAQDD-UHFFFAOYSA-N 0.000 description 1
- OAABQPJIYYMHCW-UHFFFAOYSA-N 3-amino-4-(hexadecanoylamino)benzoic acid Chemical compound NC=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCCCCCC)=O OAABQPJIYYMHCW-UHFFFAOYSA-N 0.000 description 1
- 238000010600 3H thymidine incorporation assay Methods 0.000 description 1
- LOAAZZXYDSMZRV-UHFFFAOYSA-N 4-(dodecanoylamino)-3-nitrobenzoic acid Chemical compound [N+](=O)([O-])C=1C=C(C(=O)O)C=CC1NC(CCCCCCCCCCC)=O LOAAZZXYDSMZRV-UHFFFAOYSA-N 0.000 description 1
- ZVQKZZZALXUGBT-UHFFFAOYSA-N 4-amino-3-(dodecanoylamino)benzoic acid Chemical compound NC1=C(C=C(C(=O)O)C=C1)NC(CCCCCCCCCCC)=O ZVQKZZZALXUGBT-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical compound NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 description 1
- 229940086681 4-aminobenzoate Drugs 0.000 description 1
- 102000057234 Acyl transferases Human genes 0.000 description 1
- 108700016155 Acyl transferases Proteins 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010002329 Aneurysm Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 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 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 206010048215 Xanthomatosis Diseases 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 210000002376 aorta thoracic Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002190 fatty acyls Chemical group 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ICDQUAGMQCUEMY-UHFFFAOYSA-N heptadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCC(Cl)=O ICDQUAGMQCUEMY-UHFFFAOYSA-N 0.000 description 1
- UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000001125 hyperlipoproteinemic effect Effects 0.000 description 1
- BXZBGYJQEFZICM-UHFFFAOYSA-N icosanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCC(Cl)=O BXZBGYJQEFZICM-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 229960000318 kanamycin Drugs 0.000 description 1
- 229930027917 kanamycin Natural products 0.000 description 1
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
- 229930182823 kanamycin A Natural products 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 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
- 210000003205 muscle Anatomy 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 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
- 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
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940056360 penicillin g Drugs 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
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 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
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003890 succinate salts Chemical class 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
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- JUKPJGZUFHCZQI-UHFFFAOYSA-N undecanoyl chloride Chemical compound CCCCCCCCCCC(Cl)=O JUKPJGZUFHCZQI-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil 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 |
|---|---|
| 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 (fr) |
| AU (2) | AU5954680A (fr) |
| CA (1) | CA1141765A (fr) |
| DE (2) | DE3023433A1 (fr) |
| DK (2) | DK268080A (fr) |
| ES (2) | ES8105300A1 (fr) |
| FI (2) | FI802009A (fr) |
| FR (2) | FR2459794A1 (fr) |
| GB (1) | GB2053912B (fr) |
| GR (2) | GR69291B (fr) |
| IL (2) | IL60378A0 (fr) |
| IT (2) | IT1197459B (fr) |
| LU (2) | LU82546A1 (fr) |
| NL (2) | NL8003628A (fr) |
| NO (2) | NO801875L (fr) |
| NZ (2) | NZ194122A (fr) |
| PH (1) | PH15713A (fr) |
| PT (2) | PT71444A (fr) |
| SE (2) | SE8004621L (fr) |
| YU (1) | YU163680A (fr) |
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 (fr) * | 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 IL IL60378A patent/IL60378A0/xx unknown
- 1980-06-23 NO NO801875A patent/NO801875L/no unknown
- 1980-06-23 AU AU59546/80A patent/AU5954680A/en not_active Abandoned
- 1980-06-23 DK DK268080A patent/DK268080A/da not_active Application Discontinuation
- 1980-06-23 SE SE8004621A patent/SE8004621L/xx not_active Application Discontinuation
- 1980-06-23 NZ NZ194122A patent/NZ194122A/xx unknown
- 1980-06-23 AT AT0328780A patent/ATA328780A/de not_active Application Discontinuation
- 1980-06-23 FI FI802009A patent/FI802009A/fi not_active Application Discontinuation
- 1980-06-23 IL IL60379A patent/IL60379A0/xx unknown
- 1980-06-23 DE DE19803023433 patent/DE3023433A1/de not_active Withdrawn
- 1980-06-23 ES ES492692A patent/ES8105300A1/es not_active Expired
- 1980-06-23 SE SE8004622A patent/SE8004622L/xx not_active Application Discontinuation
- 1980-06-23 CA CA000354555A patent/CA1141765A/fr not_active Expired
- 1980-06-23 DK DK267880A patent/DK267880A/da not_active Application Discontinuation
- 1980-06-23 DE DE19803023432 patent/DE3023432A1/de not_active Withdrawn
- 1980-06-23 IT IT22965/80A patent/IT1197459B/it active
- 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 PT PT71444A patent/PT71444A/fr unknown
- 1980-06-23 GB GB8020548A patent/GB2053912B/en not_active Expired
- 1980-06-23 YU YU01636/80A patent/YU163680A/xx unknown
- 1980-06-23 AU AU59545/80A patent/AU5954580A/en not_active Abandoned
- 1980-06-23 PH PH24182A patent/PH15713A/en unknown
- 1980-06-23 ES ES492693A patent/ES8105268A1/es not_active Expired
- 1980-06-23 NL NL8003627A patent/NL8003627A/nl not_active Application Discontinuation
- 1980-06-23 NZ NZ194123A patent/NZ194123A/xx unknown
- 1980-06-23 PT PT71445A patent/PT71445A/pt unknown
- 1980-06-23 NO NO801876A patent/NO801876L/no unknown
- 1980-06-23 FI FI802008A patent/FI802008A/fi not_active Application Discontinuation
- 1980-06-23 IT IT22966/80A patent/IT1131841B/it active
- 1980-06-23 FR FR8013845A patent/FR2459796A1/fr not_active Withdrawn
- 1980-06-24 LU LU82546A patent/LU82546A1/fr unknown
- 1980-06-24 LU LU82545A patent/LU82545A1/fr unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0591528B1 (fr) | DERIVE DE PYRAZOLO[1,5-a]PYRIMIDINE ET AGENT ANTI-INFLAMMATOIRECONTENANT CE DERIVE | |
| CA2237221C (fr) | Inhibiteur de la proteine kinase c | |
| US4731358A (en) | β-carbolines and their use as tranquilizers | |
| KR20010040940A (ko) | 글루코코르티코이드 선택성 소염제 | |
| RU2109743C1 (ru) | Производные галантамина и фармацевтическая композиция | |
| US4193998A (en) | 1,2,3,4,6,7-Hexahydro-11BαH-benzo[a]quinolizine-derivatives | |
| EP0009801A1 (fr) | Compositions pharmaceutiques contenant des cyanocétones polycycliques | |
| CS221808B2 (en) | Method of making the 5-phenyl-2-hydroxytetrahydrofurane | |
| NO801876L (no) | Fremgangsmaate ved fremstilling av acylaminobenzosyrederivater | |
| EP0103381A1 (fr) | Anthra(1,9-cd)pyrazol-6(2H)-ones | |
| CS270249B2 (en) | Method of purine's new derivatives production | |
| US4341781A (en) | Pyridazopyridazine derivatives | |
| US3873538A (en) | Amino-9,10-dihydro-9,10-dioxo-2-anthroic acids | |
| CS199604B2 (en) | Method of producing derivatives of 4-/2-hydroxy-3-aminopropoxy/indole | |
| DK153149B (da) | Analogifremgangsmaade til fremstilling af hydroxyaminoeburnanderivater eller farmaceutisk acceptable syreadditionssalte eller optisk aktiv isomerer deraf, samt octahydroindolokinolizin-monoesterderivater til anvendelse som udgangsmateriale ved fremgangsmaaden | |
| US4888328A (en) | Alkoxycarbonylalkylphospholipids and alkylaminocarbonylalkylphospholipids | |
| US4493843A (en) | Indole and indoline carboxylic acid compounds and method of use | |
| PL127472B1 (en) | Method of obtaining new derivatives of pyrolidine | |
| US5962454A (en) | Neovascularization inhibitor | |
| US4011221A (en) | S-inosylcysteine and a process for producing the same | |
| GB2053215A (en) | Benzimidazole derivatives | |
| IL28867A (en) | 1-adamantyl and 1-adamantylmethyl carbonates of testosterone and derivatives thereof | |
| KR920002143B1 (ko) | 5-치환 우리딘 유도체 및 그의 제조 중간체 | |
| US3865838A (en) | (5-Indolyloxy)-acetic acid compounds and therapeutic compositions | |
| US4278798A (en) | 1-Ethyl-1,4-dihydro-6-(2-naphthyl)-4-oxonicotinic acid and esters thereof |