NO751554L - - Google Patents
Info
- Publication number
- NO751554L NO751554L NO751554A NO751554A NO751554L NO 751554 L NO751554 L NO 751554L NO 751554 A NO751554 A NO 751554A NO 751554 A NO751554 A NO 751554A NO 751554 L NO751554 L NO 751554L
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- found
- hydroxycarbostyril
- acid
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 21
- -1 6,7-dimethyl-4-hydroxycarbostyril 6.7-diethyl-4-hydroxycarbostyril 7.8- dimethyl-4-hydroxycarbostyril 4-hydroxy-8-methylcarbostyril 6-ethyl-4-hydroxycarbostyril Chemical compound 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LHJYNHFFMNIQNJ-UHFFFAOYSA-N 6-ethyl-4-hydroxy-1-methylquinolin-2-one Chemical compound CN1C(=O)C=C(O)C2=CC(CC)=CC=C21 LHJYNHFFMNIQNJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 97
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 38
- 229960000583 acetic acid Drugs 0.000 description 36
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 25
- 229910017604 nitric acid Inorganic materials 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 239000012362 glacial acetic acid Substances 0.000 description 21
- 239000000725 suspension Substances 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 17
- 238000001816 cooling Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000006396 nitration reaction Methods 0.000 description 10
- 239000011734 sodium Substances 0.000 description 9
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 8
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 8
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- 150000002828 nitro derivatives Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- SPEGUNZOHLFGCL-UHFFFAOYSA-N 2-(ethylamino)benzoic acid Chemical compound CCNC1=CC=CC=C1C(O)=O SPEGUNZOHLFGCL-UHFFFAOYSA-N 0.000 description 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- RTNPPPQVXREFKX-UHFFFAOYSA-N 4-hydroxy-1-methylquinolin-2-one Chemical compound C1=CC=C2C(O)=CC(=O)N(C)C2=C1 RTNPPPQVXREFKX-UHFFFAOYSA-N 0.000 description 2
- KZPBFZJUQUXVAO-UHFFFAOYSA-N 4-hydroxy-1-phenylquinolin-2-one Chemical compound C12=CC=CC=C2C(O)=CC(=O)N1C1=CC=CC=C1 KZPBFZJUQUXVAO-UHFFFAOYSA-N 0.000 description 2
- DQFPMEMMMGZBKU-UHFFFAOYSA-N 6-bromo-4-hydroxy-1h-quinolin-2-one Chemical compound C1=C(Br)C=CC2=NC(O)=CC(O)=C21 DQFPMEMMMGZBKU-UHFFFAOYSA-N 0.000 description 2
- GOLCXWYRSKYTSP-UHFFFAOYSA-N Arsenious Acid Chemical compound O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000005606 carbostyryl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- XFKRUWXHZGOBAT-UHFFFAOYSA-N 1-benzyl-4-hydroxy-3-nitroquinolin-2-one Chemical compound C12=CC=CC=C2C(O)=C([N+]([O-])=O)C(=O)N1CC1=CC=CC=C1 XFKRUWXHZGOBAT-UHFFFAOYSA-N 0.000 description 1
- XJDDSPGDIVTMEB-UHFFFAOYSA-N 1-ethyl-4,7-dihydroxy-6-methyl-3-nitroquinolin-2-one Chemical compound OC1=C(C)C=C2C(O)=C([N+]([O-])=O)C(=O)N(CC)C2=C1 XJDDSPGDIVTMEB-UHFFFAOYSA-N 0.000 description 1
- FEQPJQLHNNQRSH-UHFFFAOYSA-N 1-ethyl-4,7-dihydroxy-6-methylquinolin-2-one Chemical compound OC1=C(C)C=C2C(O)=CC(=O)N(CC)C2=C1 FEQPJQLHNNQRSH-UHFFFAOYSA-N 0.000 description 1
- BGDQBJBWFAWHHJ-UHFFFAOYSA-N 1-ethyl-4-hydroxyquinolin-2-one Chemical compound C1=CC=C2C(O)=CC(=O)N(CC)C2=C1 BGDQBJBWFAWHHJ-UHFFFAOYSA-N 0.000 description 1
- BBEOAXDWSOBKMN-UHFFFAOYSA-N 2-(ethylamino)-5-methylbenzoic acid Chemical compound CCNC1=CC=C(C)C=C1C(O)=O BBEOAXDWSOBKMN-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- CRHGUMIAEQFWIZ-UHFFFAOYSA-N 4,7-dihydroxy-1h-quinolin-2-one Chemical compound OC1=CC(=O)NC2=CC(O)=CC=C21 CRHGUMIAEQFWIZ-UHFFFAOYSA-N 0.000 description 1
- GCCHNNJSPVCFBT-UHFFFAOYSA-N 4-hydroxy-1,8-dimethyl-3-nitroquinolin-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)N(C)C2=C1C=CC=C2C GCCHNNJSPVCFBT-UHFFFAOYSA-N 0.000 description 1
- IHHMIPDRIZHMIZ-UHFFFAOYSA-N 4-hydroxy-3-nitro-7-phenoxy-1h-quinolin-2-one Chemical compound C=1C=C2C(O)=C([N+]([O-])=O)C(=O)NC2=CC=1OC1=CC=CC=C1 IHHMIPDRIZHMIZ-UHFFFAOYSA-N 0.000 description 1
- SGSIWEJDZKSVBH-UHFFFAOYSA-N 4-hydroxy-6,7-dimethoxy-1-methylquinolin-2-one Chemical compound OC1=CC(=O)N(C)C2=C1C=C(OC)C(OC)=C2 SGSIWEJDZKSVBH-UHFFFAOYSA-N 0.000 description 1
- QRTSQODPWNDQQL-UHFFFAOYSA-N 4-hydroxy-6,8-dimethyl-1h-quinolin-2-one Chemical compound N1C(=O)C=C(O)C2=CC(C)=CC(C)=C21 QRTSQODPWNDQQL-UHFFFAOYSA-N 0.000 description 1
- NFKLJQMHTHZOIF-UHFFFAOYSA-N 4-hydroxy-6-methoxy-1,7-dimethyl-3-nitroquinolin-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)N(C)C2=C1C=C(OC)C(C)=C2 NFKLJQMHTHZOIF-UHFFFAOYSA-N 0.000 description 1
- OXSZQTDCCMODLE-UHFFFAOYSA-N 4-hydroxy-6-methyl-1h-quinolin-2-one Chemical compound N1C(O)=CC(=O)C2=CC(C)=CC=C21 OXSZQTDCCMODLE-UHFFFAOYSA-N 0.000 description 1
- TVAYPCZDZPZKFR-UHFFFAOYSA-N 4-hydroxy-7,8-dimethyl-1h-quinolin-2-one Chemical compound OC1=CC(=O)NC2=C(C)C(C)=CC=C21 TVAYPCZDZPZKFR-UHFFFAOYSA-N 0.000 description 1
- WSOMZDLQZXJOIV-UHFFFAOYSA-N 4-hydroxy-7-methoxy-3-nitro-1h-quinolin-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)NC2=CC(OC)=CC=C21 WSOMZDLQZXJOIV-UHFFFAOYSA-N 0.000 description 1
- KHGFGTMGCJBWBB-UHFFFAOYSA-N 4-hydroxy-7-methoxy-6-methyl-3-nitro-1h-quinolin-2-one Chemical compound N1C(=O)C([N+]([O-])=O)=C(O)C2=C1C=C(OC)C(C)=C2 KHGFGTMGCJBWBB-UHFFFAOYSA-N 0.000 description 1
- SVXSGNABIKVMCI-UHFFFAOYSA-N 4-hydroxy-7-methyl-3-nitro-8-propoxy-1h-quinolin-2-one Chemical compound OC1=C([N+]([O-])=O)C(=O)NC2=C1C=CC(C)=C2OCCC SVXSGNABIKVMCI-UHFFFAOYSA-N 0.000 description 1
- ISWIDMXROBFWKT-UHFFFAOYSA-N 4-hydroxy-7-methyl-8-propoxy-1H-quinolin-2-one Chemical compound OC1=CC(NC2=C(C(=CC=C12)C)OCCC)=O ISWIDMXROBFWKT-UHFFFAOYSA-N 0.000 description 1
- RQWJEWVKCVCSCP-UHFFFAOYSA-N 4-hydroxy-7-phenoxy-1H-quinolin-2-one Chemical compound C=1C=C2C(O)=CC(=O)NC2=CC=1OC1=CC=CC=C1 RQWJEWVKCVCSCP-UHFFFAOYSA-N 0.000 description 1
- DSSAJVLTBRCVQP-UHFFFAOYSA-N 5-chloro-2-(ethylamino)benzoic acid Chemical compound CCNC1=CC=C(Cl)C=C1C(O)=O DSSAJVLTBRCVQP-UHFFFAOYSA-N 0.000 description 1
- WRIRRGCIWLBVIN-UHFFFAOYSA-N 5-methyl-2-(methylamino)benzoic acid Chemical compound CNC1=CC=C(C)C=C1C(O)=O WRIRRGCIWLBVIN-UHFFFAOYSA-N 0.000 description 1
- ZYTVPPQORHMVNL-UHFFFAOYSA-N 6-benzyl-1-ethyl-4-hydroxy-3-nitroquinolin-2-one Chemical compound C1=C2C(O)=C([N+]([O-])=O)C(=O)N(CC)C2=CC=C1CC1=CC=CC=C1 ZYTVPPQORHMVNL-UHFFFAOYSA-N 0.000 description 1
- HFOLABJPPDVJGB-UHFFFAOYSA-N 6-benzyl-1-ethyl-4-hydroxyquinolin-2-one Chemical compound C1=C2C(O)=CC(=O)N(CC)C2=CC=C1CC1=CC=CC=C1 HFOLABJPPDVJGB-UHFFFAOYSA-N 0.000 description 1
- FLANGXIPXBEEJA-UHFFFAOYSA-N 6-chloro-4-hydroxy-1-methylquinolin-2-one Chemical compound C1=C(Cl)C=C2C(O)=CC(=O)N(C)C2=C1 FLANGXIPXBEEJA-UHFFFAOYSA-N 0.000 description 1
- FDFOHUPKUMVQLJ-UHFFFAOYSA-N 7-chloro-4-hydroxy-1-methylquinolin-2-one Chemical compound ClC1=CC=C2C(O)=CC(=O)N(C)C2=C1 FDFOHUPKUMVQLJ-UHFFFAOYSA-N 0.000 description 1
- XGNGQJXCUMPRHN-UHFFFAOYSA-N 7-chloro-4-hydroxy-1h-quinolin-2-one Chemical compound C1=C(Cl)C=C2NC(O)=CC(=O)C2=C1 XGNGQJXCUMPRHN-UHFFFAOYSA-N 0.000 description 1
- AAZDNCHJFDSFEP-UHFFFAOYSA-N 7-chloro-4-hydroxy-6-methoxy-1H-quinolin-2-one Chemical compound OC1=CC(=O)NC2=C1C=C(OC)C(Cl)=C2 AAZDNCHJFDSFEP-UHFFFAOYSA-N 0.000 description 1
- XZNVREAIBVPCKN-UHFFFAOYSA-N 7-ethyl-4-hydroxy-3-nitro-6-phenyl-1h-quinolin-2-one Chemical compound CCC1=CC=2NC(=O)C([N+]([O-])=O)=C(O)C=2C=C1C1=CC=CC=C1 XZNVREAIBVPCKN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CVEURVSAZSZEHY-UHFFFAOYSA-N 8-benzyl-4-hydroxy-6-methyl-1H-quinolin-2-one Chemical compound C=12NC(=O)C=C(O)C2=CC(C)=CC=1CC1=CC=CC=C1 CVEURVSAZSZEHY-UHFFFAOYSA-N 0.000 description 1
- YMZASLVENRUONX-UHFFFAOYSA-N 8-bromo-4-hydroxy-1h-quinolin-2-one Chemical compound C1=CC=C(Br)C2=NC(O)=CC(O)=C21 YMZASLVENRUONX-UHFFFAOYSA-N 0.000 description 1
- OECNFSGXQMTYMK-UHFFFAOYSA-N 8-chloro-4-hydroxy-1h-quinolin-2-one Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1Cl OECNFSGXQMTYMK-UHFFFAOYSA-N 0.000 description 1
- LHLNAMDELMMBLW-UHFFFAOYSA-N 8-ethoxy-4-hydroxy-3-nitro-6-propyl-1h-quinolin-2-one Chemical compound N1C(=O)C([N+]([O-])=O)=C(O)C2=CC(CCC)=CC(OCC)=C21 LHLNAMDELMMBLW-UHFFFAOYSA-N 0.000 description 1
- KTWUHAQIIIYFBH-UHFFFAOYSA-N 8-ethoxy-4-hydroxy-6-propyl-1H-quinolin-2-one Chemical compound C(C)OC=1C=C(C=C2C(=CC(NC=12)=O)O)CCC KTWUHAQIIIYFBH-UHFFFAOYSA-N 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 101100102510 Clonostachys rogersoniana verI gene Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 239000008364 bulk solution Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2400073A GB1453863A (en) | 1973-05-19 | 1973-05-19 | Pharmaceutical compositions comprising nitrocarbostyrils for the treatment of allergic and immunological hypersensitivity |
| GB2431773 | 1973-05-22 | ||
| NO741811 | 1974-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO751554L true NO751554L (enrdf_load_stackoverflow) | 1974-11-20 |
Family
ID=27258282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO751554A NO751554L (enrdf_load_stackoverflow) | 1973-05-19 | 1975-04-30 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO751554L (enrdf_load_stackoverflow) |
-
1975
- 1975-04-30 NO NO751554A patent/NO751554L/no unknown
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