NO801930L - Aminobenzoesyrederivater for anvendelse som mellomprodukter - Google Patents
Aminobenzoesyrederivater for anvendelse som mellomprodukterInfo
- Publication number
- NO801930L NO801930L NO801930A NO801930A NO801930L NO 801930 L NO801930 L NO 801930L NO 801930 A NO801930 A NO 801930A NO 801930 A NO801930 A NO 801930A NO 801930 L NO801930 L NO 801930L
- Authority
- NO
- Norway
- Prior art keywords
- amino
- bromo
- group
- ethyl
- carbon atoms
- Prior art date
Links
- 150000005417 aminobenzoic acid derivatives Chemical class 0.000 title claims description 8
- 239000000543 intermediate Substances 0.000 title description 4
- -1 pyrrolidino, piperidino, hexamethyleneimino, morpholino Chemical group 0.000 claims description 131
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 68
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 34
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000466 oxiranyl group Chemical group 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- AHMIRAVXLBORNM-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoate Chemical compound C1CCCCC1N(CC)CC1=CC(C(=O)OCC(O)CO)=CC(Br)=C1N AHMIRAVXLBORNM-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002366 halogen compounds Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- VVPZZBVZGPZGOS-UHFFFAOYSA-N 2-hydroxyethyl 4-amino-3-bromo-5-[[cyclohexyl(propyl)amino]methyl]benzoate Chemical compound C1CCCCC1N(CCC)CC1=CC(C(=O)OCCO)=CC(Br)=C1N VVPZZBVZGPZGOS-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 90
- 238000002844 melting Methods 0.000 description 72
- 230000008018 melting Effects 0.000 description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 36
- CIQFXTRZSGSGAU-UHFFFAOYSA-N 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoyl chloride;hydrochloride Chemical compound Cl.C1CCCCC1N(CC)CC1=CC(C(Cl)=O)=CC(Br)=C1N CIQFXTRZSGSGAU-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 238000002211 ultraviolet spectrum Methods 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000002329 infrared spectrum Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- FNPFHBFZWQPNND-UHFFFAOYSA-N 4-amino-3-bromo-5-(diethylaminomethyl)benzoyl chloride;hydrochloride Chemical compound Cl.CCN(CC)CC1=CC(C(Cl)=O)=CC(Br)=C1N FNPFHBFZWQPNND-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 230000000767 anti-ulcer Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- AVKIDCLTDUJXRP-UHFFFAOYSA-M sodium;4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoate Chemical compound [Na+].C1CCCCC1N(CC)CC1=CC(C([O-])=O)=CC(Br)=C1N AVKIDCLTDUJXRP-UHFFFAOYSA-M 0.000 description 4
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 3
- VEPMMKKALPHWAG-UHFFFAOYSA-N 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoic acid;hydrochloride Chemical compound Cl.C1CCCCC1N(CC)CC1=CC(C(O)=O)=CC(Br)=C1N VEPMMKKALPHWAG-UHFFFAOYSA-N 0.000 description 3
- RHNNZPNQTIQMQZ-UHFFFAOYSA-N Cl.NC1=C(C=C(C(=O)Cl)C=C1CN1CCOCC1)Br Chemical compound Cl.NC1=C(C=C(C(=O)Cl)C=C1CN1CCOCC1)Br RHNNZPNQTIQMQZ-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000001741 anti-phlogistic effect Effects 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- XSCFMZSKYFUFEM-UHFFFAOYSA-N 2-chloroethyl 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoate Chemical compound C1CCCCC1N(CC)CC1=CC(C(=O)OCCCl)=CC(Br)=C1N XSCFMZSKYFUFEM-UHFFFAOYSA-N 0.000 description 2
- QGZWKXQZRUWFKL-UHFFFAOYSA-N 2-hydroxyethyl 4-amino-3-bromo-5-(diethylaminomethyl)benzoate Chemical compound CCN(CC)CC1=CC(C(=O)OCCO)=CC(Br)=C1N QGZWKXQZRUWFKL-UHFFFAOYSA-N 0.000 description 2
- BVSFHZBQKVQTIS-UHFFFAOYSA-N 2-hydroxyethyl 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoate Chemical compound C1CCCCC1N(CC)CC1=CC(C(=O)OCCO)=CC(Br)=C1N BVSFHZBQKVQTIS-UHFFFAOYSA-N 0.000 description 2
- CRPRLXROADMVCP-UHFFFAOYSA-N 3-hydroxypropyl 4-amino-3-bromo-5-(diethylaminomethyl)benzoate Chemical compound CCN(CC)CC1=CC(C(=O)OCCCO)=CC(Br)=C1N CRPRLXROADMVCP-UHFFFAOYSA-N 0.000 description 2
- JLOVLPKUABJEHE-UHFFFAOYSA-N 3-hydroxypropyl 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoate Chemical compound C1CCCCC1N(CC)CC1=CC(C(=O)OCCCO)=CC(Br)=C1N JLOVLPKUABJEHE-UHFFFAOYSA-N 0.000 description 2
- QTLMJHWSPXKUIS-UHFFFAOYSA-N 4-amino-3-bromo-5-(pyrrolidin-1-ylmethyl)benzoyl chloride hydrochloride Chemical compound Cl.NC1=C(C=C(C(=O)Cl)C=C1CN1CCCC1)Br QTLMJHWSPXKUIS-UHFFFAOYSA-N 0.000 description 2
- RPCYNQITXXOEOG-UHFFFAOYSA-N 4-hydroxybutyl 4-amino-3-bromo-5-(diethylaminomethyl)benzoate Chemical compound CCN(CC)CC1=CC(C(=O)OCCCCO)=CC(Br)=C1N RPCYNQITXXOEOG-UHFFFAOYSA-N 0.000 description 2
- GLKPBHZMFUTUCY-UHFFFAOYSA-N 4-hydroxybutyl 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoate Chemical compound C1CCCCC1N(CC)CC1=CC(C(=O)OCCCCO)=CC(Br)=C1N GLKPBHZMFUTUCY-UHFFFAOYSA-N 0.000 description 2
- VQTHYKIIJSDHPI-UHFFFAOYSA-N 5-hydroxypentyl 4-amino-3-bromo-5-(diethylaminomethyl)benzoate Chemical compound CCN(CC)CC1=CC(C(=O)OCCCCCO)=CC(Br)=C1N VQTHYKIIJSDHPI-UHFFFAOYSA-N 0.000 description 2
- VJTSSDIBMBJYDA-UHFFFAOYSA-N 5-hydroxypentyl 4-amino-3-bromo-5-[[cycloheptyl(ethyl)amino]methyl]benzoate Chemical compound C1CCCCCC1N(CC)CC1=CC(C(=O)OCCCCCO)=CC(Br)=C1N VJTSSDIBMBJYDA-UHFFFAOYSA-N 0.000 description 2
- UZAFLWXFISXYCG-UHFFFAOYSA-N 5-hydroxypentyl 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoate Chemical compound C1CCCCC1N(CC)CC1=CC(C(=O)OCCCCCO)=CC(Br)=C1N UZAFLWXFISXYCG-UHFFFAOYSA-N 0.000 description 2
- BTCFKUWAPASLPB-UHFFFAOYSA-N 6-chlorohexyl 4-amino-3-bromo-5-(diethylaminomethyl)benzoate Chemical compound CCN(CC)CC1=CC(C(=O)OCCCCCCCl)=CC(Br)=C1N BTCFKUWAPASLPB-UHFFFAOYSA-N 0.000 description 2
- FGTTYAHTKNBTNP-UHFFFAOYSA-N 7-hydroxyheptyl 4-amino-3-bromo-5-[[cyclohexyl(ethyl)amino]methyl]benzoate Chemical compound C1CCCCC1N(CC)CC1=CC(C(=O)OCCCCCCCO)=CC(Br)=C1N FGTTYAHTKNBTNP-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- NRVAVWATXFWJDL-UHFFFAOYSA-N Cl.NC1=C(C=C(C(=O)Cl)C=C1CN(C)C)Br Chemical compound Cl.NC1=C(C=C(C(=O)Cl)C=C1CN(C)C)Br NRVAVWATXFWJDL-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 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
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 230000000954 anitussive effect Effects 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
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- 239000000829 suppository Substances 0.000 description 1
- MDKGKXOCJGEUJW-UHFFFAOYSA-N suprofen Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- GUHPRPJDBZHYCJ-UHFFFAOYSA-N tiaprofenic acid Chemical compound S1C(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CC=C1 GUHPRPJDBZHYCJ-UHFFFAOYSA-N 0.000 description 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792926471 DE2926471A1 (de) | 1979-06-30 | 1979-06-30 | Neue aminobenzoesaeurederivate, deren herstellung und deren verwendung als arzneimittel oder zwischenprodukte |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO801930L true NO801930L (no) | 1981-01-02 |
Family
ID=6074590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801930A NO801930L (no) | 1979-06-30 | 1980-06-27 | Aminobenzoesyrederivater for anvendelse som mellomprodukter |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5610154A (el) |
| AT (1) | AT370085B (el) |
| CA (1) | CA1140934A (el) |
| DE (1) | DE2926471A1 (el) |
| DK (1) | DK279380A (el) |
| ES (1) | ES492843A0 (el) |
| FI (1) | FI802048A (el) |
| GR (1) | GR69273B (el) |
| NO (1) | NO801930L (el) |
| PT (1) | PT71452B (el) |
-
1979
- 1979-06-30 DE DE19792926471 patent/DE2926471A1/de not_active Withdrawn
-
1980
- 1980-06-03 GR GR62112A patent/GR69273B/el unknown
- 1980-06-10 JP JP7828080A patent/JPS5610154A/ja active Pending
- 1980-06-11 AT AT0306380A patent/AT370085B/de not_active IP Right Cessation
- 1980-06-25 PT PT71452A patent/PT71452B/pt unknown
- 1980-06-27 ES ES492843A patent/ES492843A0/es active Granted
- 1980-06-27 DK DK279380A patent/DK279380A/da not_active Application Discontinuation
- 1980-06-27 NO NO801930A patent/NO801930L/no unknown
- 1980-06-27 FI FI802048A patent/FI802048A/fi not_active Application Discontinuation
- 1980-06-30 CA CA000355165A patent/CA1140934A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1140934A (en) | 1983-02-08 |
| GR69273B (el) | 1982-05-13 |
| DK279380A (da) | 1980-12-31 |
| PT71452A (de) | 1980-07-01 |
| ES8201536A1 (es) | 1981-11-16 |
| JPS5610154A (en) | 1981-02-02 |
| ATA306380A (de) | 1982-07-15 |
| AT370085B (de) | 1983-02-25 |
| FI802048A (fi) | 1980-12-31 |
| DE2926471A1 (de) | 1981-01-15 |
| ES492843A0 (es) | 1981-11-16 |
| PT71452B (de) | 1981-10-23 |
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